N-[3-(acetyl-methyl-amino)-5-amino-phenyl]-N-methyl-acetamide → HCID 19353552, compound

HRID 1584211Notes

Reaction equation

HRID 1584211 reaction equation
[C:1]([N:4]([CH3:17])[C:5]1[CH:6]=[C:7]([N:12]([CH3:16])[C:13](=[O:15])[CH3:14])[CH:8]=[C:9]([NH2:11])[CH:10]=1)(=[O:3])[CH3:2].[NH:18]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:19]([CH3:21])=[O:20].[S:28](Cl)(O)(=[O:30])=[O:29]>N1C=CC=CC=1.O>[C:19]([NH:18][C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:11][C:9]2[CH:8]=[C:7]([N:12]([CH3:16])[C:13](=[O:15])[CH3:14])[CH:6]=[C:5]([N:4]([C:1](=[O:3])[CH3:2])[CH3:17])[CH:10]=2)(=[O:30])=[O:29])=[CH:24][CH:23]=1)(=[O:20])[CH3:21]

Participants

5

Reactant 2

HCID 10776126N-[3-(acetyl-methyl-amino)-5-amino-phenyl]-N-methyl-acetamideHCID 19353479HCID 19353479, compound

Product 1

HCID 19353552HCID 19353552, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

0.15 g (0.00063 mol) of N-[3-(acetyl-methyl-amino)-5-amino-phenyl]-N-methyl-acetamide was dissolved in 3 ml of pyridine, treated with 0.154 g (0.00064 mol) of 4-acetamino-benzene-sulfochloride and stirred at room temperature for 16 hours. Subsequently, the mixture was freed from solvent, the residue was taken up in 25 ml of water, extracted four times with 200 ml of ethyl acetate each time and the combined organic phases were washed with saturated sodium chloride solution and dried over sodium sulfate. After removal of the solvent the residue was chromatographed on silica gel, firstly with 2% and then 5% methanol in dichloromethane. There was obtained 0.15 g (55%) of N-[3-(4-acetylamino-phenylsulfonylamino)-5-(acetyl-methyl-amino)-phenyl]-N-methyl-acetamide as an orange colored, amorphous solid. MS (ISN): me/e=431 (C20H23N4O5S-).

Workup

  1. extractionextracted four times with 200 ml of ethyl acetate each time
  2. washthe combined organic phases were washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of the solvent the residue
  5. customwas chromatographed on silica gel, firstly with 2%

Sources & evidence

ORD record
ord-0f71de3ff2b04fa3aa176113456c86e0
Source dataset
uspto-grants-1999_08
Patent number
US05932599

Reaction notes

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