4-Methoxy-2-nitroaniline → 2(4-Tolylsulfonyl)ethyl 4-(4-methoxy-2-nitro-phenyl)aminosulfonyl-2-(2-[4-tolylsulfonyl]ethoxycarbonylmethoxy)phenoxyacetate

HRID 1593237Notes

Reaction equation

HRID 1593237 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.Cl[S:14]([C:17]1[CH:39]=[CH:38][C:20]([O:21][CH2:22][C:23]([O:25][CH2:26][CH2:27][S:28]([C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=2)(=[O:30])=[O:29])=[O:24])=[C:19]([O:40][CH2:41][C:42]([O:44][CH2:45][CH2:46][S:47]([C:50]2[CH:55]=[CH:54][C:53]([CH3:56])=[CH:52][CH:51]=2)(=[O:49])=[O:48])=[O:43])[CH:18]=1)(=[O:16])=[O:15]>N1C=CC=CC=1.C1(C)C=CC=CC=1.ClCCl>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH:7][S:14]([C:17]2[CH:39]=[CH:38][C:20]([O:21][CH2:22][C:23]([O:25][CH2:26][CH2:27][S:28]([C:31]3[CH:32]=[CH:33][C:34]([CH3:37])=[CH:35][CH:36]=3)(=[O:29])=[O:30])=[O:24])=[C:19]([O:40][CH2:41][C:42]([O:44][CH2:45][CH2:46][S:47]([C:50]3[CH:55]=[CH:54][C:53]([CH3:56])=[CH:52][CH:51]=3)(=[O:49])=[O:48])=[O:43])[CH:18]=2)(=[O:15])=[O:16])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1

Participants

6

Reactant 2

HCID 667934-Methoxy-2-nitroanilineHCID 224793092-(4-Tolylsulfonyl)ethyl 4-chlorosulfonyl-2-(2-[4-tolylsulfonyl]ethoxycarbonylmethoxy)phenoxyacetate

Product 1

HCID 224793242(4-Tolylsulfonyl)ethyl 4-(4-methoxy-2-nitro-phenyl)aminosulfonyl-2-(2-[4-tolylsulfonyl]ethoxycarbonylmethoxy)phenoxyacetateYield 58.3%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

4-Methoxy-2-nitroaniline (2.3 g, 0.014 mol) and 2-(4-tolylsulfonyl)ethyl 4-chlorosulfonyl-2-(2-[4-tolylsulfonyl]ethoxycarbonylmethoxy)phenoxyacetate (Intermediate A16, 9.6 g, 0.014 mol) were dissolved in 40 mL of pyridine and stirred under positive nitrogen pressure. After ca. 16 hr, the mixture was diluted with 50 mL of toluene and 20 mL of dichloromethane and was concentrated at aspirator pressure. The residue was purified on a flash silica gel column (dichloromethane→5:1 dichloromethane:ethyl acetate) to yield 6.7 g (58%) of the title compound.

Workup

  1. concentrationwas concentrated at aspirator pressure
  2. customThe residue was purified on a flash silica gel column (dichloromethane→5:1 dichloromethane:ethyl acetate)

Sources & evidence

ORD record
ord-d49115c07c7741068e43baf916d42c4f
Source dataset
uspto-grants-2007_11
Patent number
US07294716B2

Reaction notes

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