Dichloromethane → 2-benzoyl-N-[2-(p-toluenesulfonamido)ethyl]-N-isopropylbenzamide

HRID 1579539Notes

Reaction equation

HRID 1579539 reaction equation
[C:1]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCl.[CH:21]([NH:24][CH2:25][CH2:26][NH:27][S:28]([C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=1)(=[O:30])=[O:29])([CH3:23])[CH3:22]>C(N(CC)CC)C>[C:1]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([N:24]([CH2:25][CH2:26][NH:27][S:28]([C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=1)(=[O:30])=[O:29])[CH:21]([CH3:22])[CH3:23])=[O:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 68132-Benzoylbenzoic AcidHCID 21568614N-[2-(isopropylamino)ethyl]-p-toluenesulfonamide

Product 1

HCID 537590362-benzoyl-N-[2-(p-toluenesulfonamido)ethyl]-N-isopropylbenzamide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of 37 grams of ψ-acid chloride of 0-benzoyl benzoic acid in 60 ml. of dichloromethane was added dropwise to a stirred solution of 38.5 grams of N-[2-(isopropylamino) ethyl]-p-toluenesulfonamide, 200 ml. of dichloromethane and 25 ml. of triethylamine. The mixture was refluxed for 3.5 hours. After cooling, the solution was extracted successively with water, 10% hydrochloric acid, and saturated sodium carbonate solution. The dichloromethane solution was dried over magnesium sulfate and the solvent evaporated in vacuo to a solid residue. On recrystallization from ethyl acetate there was obtained 2-benzoyl-N-[2-(p-toluenesulfonamido)ethyl]-N-isopropylbenzamide, m.p. 135°-137°C.

Workup

  1. temperatureThe mixture was refluxed for 3.5 hours
  2. temperatureAfter cooling
  3. extractionthe solution was extracted successively with water, 10% hydrochloric acid, and saturated sodium carbonate solution
  4. dry with materialThe dichloromethane solution was dried over magnesium sulfate
  5. customthe solvent evaporated in vacuo to a solid residue
  6. customOn recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-13f7c8a9f74244558866f4ef2dc7d38a
Source dataset
uspto-grants-1976_01
Patent number
US03931218

Reaction notes

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