Benzylamine → (4-Benzylsulfamoyl-2-nitro-phenyl)-carbamic acid ethyl ester

HRID 2182431Notes

Reaction equation

HRID 2182431 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:8][C:7]=1[N+:16]([O-:18])=[O:17])[CH3:2].C(N(C(C)C)CC)(C)C.[CH2:29]([NH2:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>ClCCl>[CH2:1]([O:3][C:4](=[O:19])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([S:12](=[O:14])(=[O:13])[NH:36][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:8][C:7]=1[N+:16]([O-:18])=[O:17])[CH3:2]

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 12963055(4-Chlorosulfonyl-2-nitro-phenyl)-carbamic acid ethyl ester

Product 1

HCID 20784934(4-Benzylsulfamoyl-2-nitro-phenyl)-carbamic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4-chlorosulfonyl-2-nitro-phenyl)-carbamic acid ethyl ester (2 g, Reference Example 63) in dichloromethane (50 ml) at 0° C., under a nitrogen atmosphere, was added diisopropylethylamine (2.71 ml) and benzylamine (0.850 ml). The reaction was warmed to ambient temperature and stirred for 12 hours. The reaction mixture was then washed with water (2×20 ml) and brine (2×20 ml), dried over magnesium sulfate, filtered and the filtrate concentrated in vacuo to give the title compound (2.29 g) as a brown solid. LC-MS (METHOD J): RT=3.83 minutes, 380.12 (M+H)+.

Workup

  1. washThe reaction mixture was then washed with water (2×20 ml) and brine (2×20 ml)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-6599fcbb68d54d008bfaf93f9b81cafc
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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