37560-50-2|1-(4-Chlorophenyl)-1H-pyrrole-2-carbaldehyde| Ambeed

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CAS No. :	37560-50-2
Formula :	C₁₁H₈ClNO
M.W :	205.64
SMILES Code :	O=CC1=CC=CN1C2=CC=C(Cl)C=C2
MDL No. :	MFCD00174283

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Yield	Reaction Conditions	Operation in experiment
	With sodium cyanoborohydride; acetic acid; In methanol; at 20℃; for 18h;	1-4-(Chlorophenyl)-1H-pyrrole-2-carboxaldehyde (1 eqv.) and pyrrolidin-2-yl-methanol (2 eqv.) are dissolved in 2percent AcOH in MeOH, and NaCNBH3 (3 eqv.) is added. The mixture is stirred at room temperature for 18 h and subsequently evaporated and purified by flash chromatography to give the alcohol.
	With sodium cyanoborohydride; acetic acid; In methanol; at 20℃; for 18h;	Example 6 - Synthesis of N-{l-[l-(4-chlorophenyl)-pyrrol-2-ylmethyl]-pyrrolidin-2- ylmethylene amino}-N',N',N"-triethyl guanidine.l-(4-chlorophenyl)-pyrrole-2-carboxaldehyde (411 mg, 2 mmol) and pyrrolidin-2-yl- methanol (404 mg, 4 mmol) are dissolved in 2percent AcOH in MeOH and NaCNBH3 (378 mg, 6 mmol) is added. The solution is stirred at room temperature for 18 hr. evaporated and purified by flash chromatography to give {l-[l-(4-Chloro-phenyl)-pyrrol-2-ylmethyl]- pyrrolidin-2-yl}-methanol. The alcohol (1 eqv.) is dissolved in DMSO: DCM (3: 1).Triethylamine (5 eq.) and subsequently SO3-pyridine complex (5 eqv.) are added and the reaction mixture is stirred at room temperature for 1 h. The mixture is diluted with H2O and extracted with EtOAc. The combined layers are washed with 1 N HCI and brine, dried (Na2SO4), filtered and evaporated in vacuo to give crude l-[l-(4-chlorophenyl)-pyrrol-2- ylmethyl]-pyrrolidine-2-carbaldehyde.Diethylthiocarbamoyl chloride (198 mg, 1.3 mmol) and hydrazine monohydrate (65 mg, 1.3 mmol) are mixed in ethanol (3 ml). The mixture is stirred at room temperature until the acid chloride is consumed. Methyl iodide is added (185 mg, 1.3 mmol) and the reaction <n="78"/>mixture is stirred at room temperature. The solvent is removed in vacuo to give crude 4,4- diethyl-S-methyl-isothiosemicarbazide hydroiodide, which is mixed with crude l-[l-(4- Chloro-phenyl)-pyrrol-2-ylmethyl]-pyrrolidine-2-carbaldehyde prepared as described above (289 mg, 1 mmol) in ethanol (5 ml) and heated at reflux. When the aldehyde is consumed the solvent is removed. The residue is suspended in dry toluene (5 ml) and a solution of ethylamine (3 mmol) in dry toluene (1 ml) is added. The mixture is heated at reflux in a sealed vial until completion of the reaction. The solvent is removed and the solid residue is recrystallized to give the title product. The synthesis is illustrated in Fig. 9.

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CAS No.: 37560-50-2

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CAS No.: 37560-50-2

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[ 37560-50-2 ] Synthesis Path-Downstream 1~1

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed