Hydrochloric Acid → 3-Chloro-4-(pyrrolidin-1-ylsulfonyl)benzonitrile

HRID 2053923Notes

Reaction equation

HRID 2053923 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=1[S:10](Cl)(=[O:12])=[O:11].[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[S:10]([N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)(=[O:12])=[O:11])[C:8]#[N:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 27357222-Chloro-4-cyanobenzene-1-sulfonyl chloride

Product 1

HCID 693125003-Chloro-4-(pyrrolidin-1-ylsulfonyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

900 mg (4 mmol) of 2-chloro-4-cyanobenzenesulfonic acid chloride is dissolved in 3 mL of pyridine and, after the addition of 0.5 mL (5.8 mmol) of pyrrolidine, stirred for one hour at 80° C. Then the mixture is cooled, mixed with ice, and adjusted to pH 5-6 with 1 molar hydrochloric acid. The precipitate formed is suction filtered, washed with water and dried. Yield: 1.1 g (100% of theory); Rf value: 0.20 (silica gel; petroleum ether/ethyl acetate=4:1).

Workup

  1. temperatureThen the mixture is cooled
  2. additionmixed with ice
  3. customThe precipitate formed
  4. filtrationfiltered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-3b00fd508f5847b9828189c119564c17
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

Loading…