N-methyl-2-pyrrolidone → HCID 21491925, compound

HRID 1973540Notes

Reaction equation

HRID 1973540 reaction equation
Br[C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[CH:6][C:5]([S:11]([NH2:14])(=[O:13])=[O:12])=[C:4]([CH:15]([CH3:17])[CH3:16])[CH:3]=1.[CH3:18][N:19]1CCCC1=O>O>[C:18]([C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[CH:6][C:5]([S:11]([NH2:14])(=[O:13])=[O:12])=[C:4]([CH:15]([CH3:17])[CH3:16])[CH:3]=1)#[N:19]

Participants

4

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 21491943HCID 21491943, compound

Product 1

HCID 21491925HCID 21491925, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A one-liter flask containing 92 parts of 4-bromo-2,5-diisopropylbenzenesulfonamide, 30 parts of cuprous cyanide, and 250 parts N-methylpyrrolidone is heated at 190°-200° for 2 hours. The reaction mixture is cooled to 100° and is then poured into 1000 parts water. The precipitated material is filtered. It is heated for 2 hours near reflux with 1000 parts water and 30 parts sodium cyanide. The reaction is cooled and the precipitate filtered to obtain 60 parts 4-cyano-2,5-diisopropylbenzenesulfonamide. The solid can be recrystallized from methanol, and then exhibits a m.p. of 200°-202°.

Workup

  1. temperatureis heated at 190°-200° for 2 hours
  2. temperatureThe reaction mixture is cooled to 100°
  3. filtrationThe precipitated material is filtered
  4. temperatureIt is heated for 2 hours
  5. temperaturenear reflux with 1000 parts water and 30 parts sodium cyanide
  6. temperatureThe reaction is cooled
  7. filtrationthe precipitate filtered

Sources & evidence

ORD record
ord-5122f9f09e584cd7ab0a5732d1494eb9
Source dataset
uspto-grants-1976_12
Patent number
US03997603

Reaction notes

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