P-Anisidine → HCID 40687864, compound

HRID 2094915Notes

Reaction equation

HRID 2094915 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.C(N(CC)CC)C.Cl[S:18]([C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=1)(=[O:20])=[O:19]>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:18]([C:21]2[CH:22]=[CH:23][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:29][CH:30]=2)(=[O:20])=[O:19])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 8471TriethylamineHCID 4738388Methyl 4-(Chlorosulfonyl)benzoate

Product 1

HCID 40687864HCID 40687864, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 4-methoxybenzenamine (580 mg, 4.71 mmol) and triethylamine (1.48 mL, 10.7 mmol) in dichloromethane (10 mL) was added methyl 4-(chlorosulfonyl)benzoate (1.00 g, 4.28 mmol). This mixture was stirred for 16 hours at room temperature. The reaction was diluted with dichloromethane (50 mL) and washed consecutively with water, 10% citric acid, and brine. The organics were dried over sodium sulfate and concentrated via rotovap. The resulting crude material was chromatographed on silica gel using 100% dichloromethane as eluent affording Methyl 4-(N-(4-methoxyphenyl)sulfamoyl)benzoate as a white crystalline solid (400 mg, 30% yield)

Workup

  1. washwashed consecutively with water, 10% citric acid, and brine
  2. dry with materialThe organics were dried over sodium sulfate
  3. concentrationconcentrated via rotovap
  4. customThe resulting crude material was chromatographed on silica gel using 100% dichloromethane as eluent

Sources & evidence

ORD record
ord-f146472d03f149839c59fd46553093af
Source dataset
uspto-grants-2013_05
Patent number
US08445692B2

Reaction notes

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