Dimethylformamide → HCID 13669280, compound

HRID 1183794Notes

Reaction equation

HRID 1183794 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[C:7](=O)[NH:8][S:9][C:5]=2[CH:4]=1.CN(C)C=O.S(Cl)([Cl:20])=O>ClC1C=CC=CC=1>[Cl:20][C:7]1[C:6]2[CH:11]=[CH:12][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[S:9][N:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 17892660HCID 17892660, compound

Product 1

HCID 13669280HCID 13669280, compoundYield 88%

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 90.6 g (0.5 mol) of 6-methoxy-1,2-benzisothiazol-3-one, 109.6 g (1.5 mol) of N,N-dimethylformamide and 150.0 g of chlorobenzene. While stirring, 89.2 g (0.75 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 5 hours. After terminating the reaction, the liquid reaction mixture was concentrated, and a crude product obtained was recrystallized from cyclohexane to give 86.9 g (0.44 mol) of 3-chloro-6-methoxy-1,2-benzisothiazole. The yield based on 6-methoxy-1,2-benzisothiazol-3-one was 87%.

Workup

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

Sources & evidence

ORD record
ord-8250045f84ab4924a7d66a45015bf3c3
Source dataset
uspto-grants-2014_03
Patent number
US08664404B2

Reaction notes

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