Asulam → Methyl 4-(3-(3,4-dichlorobenzyl)ureido)phenylsulfonylcarbamate

HRID 333692

Reaction equation

HRID 333692 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12](=[O:15])[O:13][CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[Cl:25][C:26]1[CH:27]=[C:28]([CH:33]=[CH:34][C:35]=1[Cl:36])[CH2:29][N:30]=[C:31]=[O:32]>C(#N)C>[Cl:25][C:26]1[CH:27]=[C:28]([CH:33]=[CH:34][C:35]=1[Cl:36])[CH2:29][NH:30][C:31](=[O:32])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12](=[O:15])[O:13][CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 18752AsulamHCID 81531DiisopropylethylamineHCID 27333681,2-Dichloro-4-(isocyanatomethyl)benzene

Product 1

HCID 25120648Methyl 4-(3-(3,4-dichlorobenzyl)ureido)phenylsulfonylcarbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of methyl 4-aminophenylsulfonylcarbamate (50 mg, 0.2 mmol), N,N-diisopropylethylamine (35 L, 0.2 mmol), 3,4-dichlorobenzylisocyanate (30 L, 0.2 mmol) in acetonitrile was stirred under an N2 atmosphere for 19 h. The mixture was concentrated and the residue purified by reverse phase HPLC using 10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA) to give methyl 4-(3-(3,4-dichlorobenzyl)ureido)phenylsulfonylcarbamate. LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=431.01; tR=2.9 min.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue purified by reverse phase

Sources & evidence

ORD record
ord-4717ed95419a4007a1a499480128a54d
Source dataset
uspto-grants-2014_11
Patent number
US08883766B2

Linked notes

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