Phenyl chloroformate → HCID 53699109, compound

HRID 862143Notes

Reaction equation

HRID 862143 reaction equation
Cl.[NH2:2][C:3]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:4]=1[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]2[O:15][CH2:16][O:17][C:11]=2[CH:10]=1)=[O:6].[C:23](Cl)(=[O:31])[O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(C(C)C)CC)(C)C>O1CCCC1>[Cl:22][C:19]1[CH:20]=[CH:21][C:3]([NH:2][C:23]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:31])=[C:4]([CH:18]=1)[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]2[O:15][CH2:16][O:17][C:11]=2[CH:10]=1)=[O:6]

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 81531DiisopropylethylamineHCID 19701934HCID 19701934, compound

Product 1

HCID 53699109HCID 53699109, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-5-chloro-N-(3,4-methylenedioxybenzyl)benzamide hydrochloride (100 mg) was reacted with 50 μl of phenyl chlorocarbonate in 5 ml of tetrahydrofuran in the presence of 150 μl of diisopropylethylamine. The reaction mixture was subjected to extraction with ethyl acetate and water and recrystallization from ethyl acetate/hexane to give 110 mg of 5-chloro-N-(3,4-methylenedioxybenzyl)-2-phenoxycarbonylaminobenzamide (yield: 88%).

Workup

  1. extractionThe reaction mixture was subjected to extraction with ethyl acetate and water and recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-7325851ce22141cd8099aa769d02380b
Source dataset
uspto-grants-1998_02
Patent number
US05716993

Reaction notes

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