Dimethylformamide → 1,2-Benzisothiazole, 3-chloro-7-nitro-

HRID 1183795Notes

Reaction equation

HRID 1183795 reaction equation
[N+:1]([C:4]1[C:12]2[S:11][NH:10][C:9](=O)[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].CN(C)C=O.S(Cl)([Cl:21])=O>ClC1C=CC=CC=1>[Cl:21][C:9]1[C:8]2[CH:7]=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[C:12]=2[S:11][N:10]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 14064459HCID 14064459, compound

Product 1

HCID 1982321,2-Benzisothiazole, 3-chloro-7-nitro-Yield 86%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A 1 L four-neck flask equipped with a stirrer, a thermometer and a condenser tube was charged with 98.1 g (0.5 mol) of 7-nitro-1,2-benzisothiazol-3-one, 146.2 g (2 mol) of N,N-dimethylformamide and 500.0 g of chlorobenzene. While stirring, 119.0 g (1.0 mol) of thionyl chloride was added dropwise thereto at 80° to 90° C. over 1 hour, and the mixture was reacted at the same temperature for 3 hours. After terminating the reaction, the liquid reaction mixture was concentrated, and a crude product obtained was recrystallized from toluene to give 91.2 g (0.43 mol) of 3-chloro-7-nitro-1,2-benzisothiazole. The yield based on 7-nitro-1,2-benzisothiazol-3-one was 85%.

Workup

  1. customA 1 L four-neck flask equipped with a stirrer
  2. customthe mixture was reacted at the same temperature for 3 hours
  3. customAfter terminating
  4. customthe reaction
  5. customthe liquid reaction mixture
  6. concentrationwas concentrated
  7. customa crude product obtained
  8. customwas recrystallized from toluene

Sources & evidence

ORD record
ord-f1c8cfbc1ead409abfd69c63eb2dabfc
Source dataset
uspto-grants-2014_03
Patent number
US08664404B2

Reaction notes

Loading…