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Chemical Structure| 623564-41-0
Chemical Structure| 623564-41-0
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CAS No. :623564-41-0 MDL No. :
Formula : C4H9ClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 136.58 Pubchem ID :-
Synonyms :

Safety of [ 623564-41-0 ]

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Application In Synthesis of [ 623564-41-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 623564-41-0 ]
  • Downstream synthetic route of [ 623564-41-0 ]

[ 623564-41-0 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 623564-41-0 ]
  • [ 623564-42-1 ]
  • [ 623564-43-2 ]
YieldReaction ConditionsOperation in experiment
36.3%
Stage #1: With toluene-4-sulfonic acid; isopropyl alcohol In cyclohexane at 80℃;
Stage #2: With sodium methylate In methanol; ethanol at 20℃; for 2 h;
Stage #3: With triethylamine In chloroform for 2 h; Heating / reflux
Step 5: 5,6-Dihydro-8H-imidazo[2,1-c][1,4]oxazine-2-carbaldehyde (9) and 56- dihvdro-8H-imidazof2, 1-clf1, 410xazine-3-carbaldehYde; The mixture of 2-bromo-3-hydroxypropenal (4.1 g), p-toluenesulfonic acid monohydrate (52 mg) and 2-propanol (5.2 mL) in cyclohexane (42 mL) was azeotroped until the vapor temperature rose to 80°C. The reaction mixture was concentrated under reduce pressure. The residue was dissolved in dry ethanol (50 mL). A mixture of the dry ethanol (200 mL) solution of 3-iminomorpholin hydrochloride (3.4 g) and 28percent methanol solution of sodium methylat (4.8 g) was added at room temperature. The reaction mixture was stirred at room temperature for 2 h, and then the reaction solvent was removed in vacuo. The residue was dissolved in chloroform (125 mL) and triethylamine (3.5 mL) was added, then the reaction mixture was heated to reflux for 2 h. The reaction mixture was cooled to room temperature and then concentrated under reduce pressure. The residue was dissolved in dichloromethane (300 mL) and washed with 50percent K2CO3 aqueous solution (2 x 100 mL). The organic layer was dried (MgS04) and filtered. The filtrate was concentrated under reduce pressure. The residue was applied to silica gel column chromatography and eluted with CHCI3-acetone (4: 1) to obtain the title (pale orange solid, 1.4 g, 36.3percent) and the other regio isomer. (pale orange solid, 609 mg, 16. 1percent). Desired product :'H NMR (CDCI3) 8 4.08-4. 15 (m, 4H), 4.88 (s, 2H), 7.58 (s, 1H), 9.85 (s, 1H). The unwanted regio isomer :'H NMR (CDCI3) 8 4.06 (t, 2H, J = 5.2 Hz), 4.40 (t, 2H, J = 5. 2 Hz), 4.90 (s, 2H), 7.75 (s, 1H), 9.72 (s, 1H).
Reference: [1] Patent: WO2003/93279, 2003, A1, . Location in patent: Page/Page column 65-66
  • 2
  • [ 623564-41-0 ]
  • [ 19263-02-6 ]
  • [ 623564-42-1 ]
  • [ 623564-43-2 ]
YieldReaction ConditionsOperation in experiment
36.3%
Stage #1: With toluene-4-sulfonic acid In cyclohexane; isopropyl alcohol at 80℃;
Stage #2: With sodium methylate In methanol; ethanol at 20℃; for 2 h;
Stage #3: With triethylamine In chloroform for 2 h; Heating / reflux
Step 5: 5. 6-Dihvdro-8H-imidazor2. 1-c1r1. 41oxazine-2-carbaldehyde (9) and 5, 6- dihydro-8H-imidazor2, 1-c1r1, 41Oxazine-3-carbaldehvde The mixture of 2-bromo-3-hydroxypropenal (4.1 g), p-toluenesulfonic acid monohydrate (52 mg) and 2-propanol (5.2 mL) in cyclohexane (42 mL) was azeotroped until the vapor temperature rose to 80°C. The reaction mixture was concentrated under reduce pressure. The residue was dissolved in dry ethanol (50 mL). A mixture of the dry ethanol (200 mL) solution of 3-iminomorpholin hydrochloride (3.4 g) and 28percent methanol solution of sodium methylat (4.8 g) was added at room temperature. The reaction mixture was stirred at room temperature for 2 h, and then the reason solvent was removed in vacuo. The residue was dissolved in chloroform (125 mL) and triethylamine (3.5 mL) was added, then the reaction mixture was heated to reflux for 2 h. The reaction mixture was cooled to room temperature and then concentrated under reduce pressure. The residue was dissolved in dichloromethane (300 mL) and washed with 50percent K2CO3 aqueous solution (2 x 100 mL). The organic layer was dried (MgS04) and filtered. The filtrate was concentrated under reduce pressure. The residue was applied to silica gel column chromatography and eluted with CHCI3-acetone (4: 1) to obtain the title (pale orange solid, 1.4 g, 36.3percent) and the other regio isomer. (pale orange solid, 609 mg, 16. 1percent). Desired product : 1H NMR (CDCI3) 5 4.08-4. 15 (m, 4H), 4.88 (s, 2H), 7.58 (s, 1H), 9.85 (s, 1H). The unwanted regio isomer :'H NMR (CDCI3) 8 4.06 (t, 2H, J = 5.2 Hz), 4.40 (t, 2H, J = 5. 2 Hz), 4.90 (s, 2H), 7.75 (s, 1H), 9.72 (s, 1H).
Reference: [1] Patent: WO2003/93277, 2003, A1, . Location in patent: Page/Page column 93-94
  • 3
  • [ 623564-41-0 ]
  • [ 623564-42-1 ]
  • [ 623564-43-2 ]
Reference: [1] Patent: US2006/276445, 2006, A1, . Location in patent: Page/Page column 17-18
  • 4
  • [ 623564-41-0 ]
  • [ 155272-73-4 ]
  • [ 623564-42-1 ]
  • [ 623564-43-2 ]
Reference: [1] Patent: WO2007/16134, 2007, A1, . Location in patent: Page/Page column 37; 38
  • 5
  • [ 623564-41-0 ]
  • [ 623564-42-1 ]
  • [ 623564-43-2 ]
YieldReaction ConditionsOperation in experiment
36.3%
Stage #1: With toluene-4-sulfonic acid; isopropyl alcohol In cyclohexane at 80℃;
Stage #2: With sodium methylate In methanol; ethanol at 20℃; for 2 h;
Stage #3: With triethylamine In chloroform for 2 h; Heating / reflux
Step 5: 5,6-Dihydro-8H-imidazo[2,1-c][1,4]oxazine-2-carbaldehyde (9) and 56- dihvdro-8H-imidazof2, 1-clf1, 410xazine-3-carbaldehYde; The mixture of 2-bromo-3-hydroxypropenal (4.1 g), p-toluenesulfonic acid monohydrate (52 mg) and 2-propanol (5.2 mL) in cyclohexane (42 mL) was azeotroped until the vapor temperature rose to 80°C. The reaction mixture was concentrated under reduce pressure. The residue was dissolved in dry ethanol (50 mL). A mixture of the dry ethanol (200 mL) solution of 3-iminomorpholin hydrochloride (3.4 g) and 28percent methanol solution of sodium methylat (4.8 g) was added at room temperature. The reaction mixture was stirred at room temperature for 2 h, and then the reaction solvent was removed in vacuo. The residue was dissolved in chloroform (125 mL) and triethylamine (3.5 mL) was added, then the reaction mixture was heated to reflux for 2 h. The reaction mixture was cooled to room temperature and then concentrated under reduce pressure. The residue was dissolved in dichloromethane (300 mL) and washed with 50percent K2CO3 aqueous solution (2 x 100 mL). The organic layer was dried (MgS04) and filtered. The filtrate was concentrated under reduce pressure. The residue was applied to silica gel column chromatography and eluted with CHCI3-acetone (4: 1) to obtain the title (pale orange solid, 1.4 g, 36.3percent) and the other regio isomer. (pale orange solid, 609 mg, 16. 1percent). Desired product :'H NMR (CDCI3) 8 4.08-4. 15 (m, 4H), 4.88 (s, 2H), 7.58 (s, 1H), 9.85 (s, 1H). The unwanted regio isomer :'H NMR (CDCI3) 8 4.06 (t, 2H, J = 5.2 Hz), 4.40 (t, 2H, J = 5. 2 Hz), 4.90 (s, 2H), 7.75 (s, 1H), 9.72 (s, 1H).
Reference: [1] Patent: WO2003/93279, 2003, A1, . Location in patent: Page/Page column 65-66
  • 6
  • [ 623564-41-0 ]
  • [ 19263-02-6 ]
  • [ 623564-42-1 ]
  • [ 623564-43-2 ]
YieldReaction ConditionsOperation in experiment
36.3%
Stage #1: With toluene-4-sulfonic acid In cyclohexane; isopropyl alcohol at 80℃;
Stage #2: With sodium methylate In methanol; ethanol at 20℃; for 2 h;
Stage #3: With triethylamine In chloroform for 2 h; Heating / reflux
Step 5: 5. 6-Dihvdro-8H-imidazor2. 1-c1r1. 41oxazine-2-carbaldehyde (9) and 5, 6- dihydro-8H-imidazor2, 1-c1r1, 41Oxazine-3-carbaldehvde The mixture of 2-bromo-3-hydroxypropenal (4.1 g), p-toluenesulfonic acid monohydrate (52 mg) and 2-propanol (5.2 mL) in cyclohexane (42 mL) was azeotroped until the vapor temperature rose to 80°C. The reaction mixture was concentrated under reduce pressure. The residue was dissolved in dry ethanol (50 mL). A mixture of the dry ethanol (200 mL) solution of 3-iminomorpholin hydrochloride (3.4 g) and 28percent methanol solution of sodium methylat (4.8 g) was added at room temperature. The reaction mixture was stirred at room temperature for 2 h, and then the reason solvent was removed in vacuo. The residue was dissolved in chloroform (125 mL) and triethylamine (3.5 mL) was added, then the reaction mixture was heated to reflux for 2 h. The reaction mixture was cooled to room temperature and then concentrated under reduce pressure. The residue was dissolved in dichloromethane (300 mL) and washed with 50percent K2CO3 aqueous solution (2 x 100 mL). The organic layer was dried (MgS04) and filtered. The filtrate was concentrated under reduce pressure. The residue was applied to silica gel column chromatography and eluted with CHCI3-acetone (4: 1) to obtain the title (pale orange solid, 1.4 g, 36.3percent) and the other regio isomer. (pale orange solid, 609 mg, 16. 1percent). Desired product : 1H NMR (CDCI3) 5 4.08-4. 15 (m, 4H), 4.88 (s, 2H), 7.58 (s, 1H), 9.85 (s, 1H). The unwanted regio isomer :'H NMR (CDCI3) 8 4.06 (t, 2H, J = 5.2 Hz), 4.40 (t, 2H, J = 5. 2 Hz), 4.90 (s, 2H), 7.75 (s, 1H), 9.72 (s, 1H).
Reference: [1] Patent: WO2003/93277, 2003, A1, . Location in patent: Page/Page column 93-94
  • 7
  • [ 623564-41-0 ]
  • [ 623564-42-1 ]
  • [ 623564-43-2 ]
Reference: [1] Patent: US2006/276445, 2006, A1, . Location in patent: Page/Page column 17-18
  • 8
  • [ 623564-41-0 ]
  • [ 155272-73-4 ]
  • [ 623564-42-1 ]
  • [ 623564-43-2 ]
Reference: [1] Patent: WO2007/16134, 2007, A1, . Location in patent: Page/Page column 37; 38
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