Benzyl Chloride → HCID 19598386, compound

HRID 1957401Notes

Reaction equation

HRID 1957401 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:6][CH:5]=1)([OH:3])=[O:2].[CH2:21](Cl)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH2:21]([O:2][C:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:8][CH:9]=1)=[O:3])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 81531DiisopropylethylamineHCID 5613854-[(4-Methylbenzene-1-sulfonyl)amino]benzoic acid

Product 1

HCID 19598386HCID 19598386, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 11.64 g (40 mmol) of N-(4-carboxyphenyl)-4-toluenesulfonamide, 5.06 g (40 mmol) of benzyl chloride and 5.20 g (44 mmol) of di-i-propylethylamine in 100 ml of dimethylformamide is heated at 140° C. for 4 hours. After the reaction is complete, the mixture is evaporated in vacuo, the residue is taken up in propyl acetate, and the solution is washed 2× with 2N hydrochloric acid and ##STR22## 2× with saturated NaHCO3 solution, dried over sodium sulfate and evaporated. 11.8 g (78% of theory) of N-(4-benzyloxycarbonylphenyl)-4-toluenesulfonamide, which are recrystallized from methanol, are obtained.

Workup

  1. customthe mixture is evaporated in vacuo
  2. washthe solution is washed 2× with 2N hydrochloric acid and ##STR22## 2× with saturated NaHCO3 solution
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. custom11.8 g (78% of theory) of N-(4-benzyloxycarbonylphenyl)-4-toluenesulfonamide, which are recrystallized from methanol
  6. customare obtained

Sources & evidence

ORD record
ord-ab4012eee8144422884f7904dbe4e96f
Source dataset
uspto-grants-1998_07
Patent number
US05783696

Reaction notes

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