Acetonitrile → HCID 19210610, compound

HRID 980787Notes

Reaction equation

HRID 980787 reaction equation
C(#N)C.[C:4]1([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:12])=[O:11])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CO.O>[C:4]1([S:10]([N:13]([C:28](=[O:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:14]2[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=2)(=[O:12])=[O:11])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 238717N-(4-Methylphenyl)benzenesulfonamide

Product 1

HCID 19210610HCID 19210610, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

250 ml of an acetonitrile solution containing 60 g (0.24 mole) of N-benzenesulfonyl-p-toluidine synthesized by the same method as in Synthesis Example 1 and 37 ml (0.27 mole) of triethylamine was cooled to below 10° C. and while maintaining this temperature, 35.8 g (0.26 mole) of benzoyl chloride was added dropwise. After the addition, the mixture was further reacted at room temperature for 30 minutes. The reaction mixture was then added to 1 liter of water. The precipitate was collected by filtration, washed with water and then with methanol to give 80.8 g (0.23 mole) of the captioned compound.

Workup

  1. temperaturewas cooled to below 10° C.
  2. additionwas added dropwise
  3. additionAfter the addition
  4. customthe mixture was further reacted at room temperature for 30 minutes
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-b41d6d023c6640419aab9aa37296d3f7
Source dataset
uspto-grants-1987_01
Patent number
US04639408

Reaction notes

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