Dimethylformamide → HCID 57879640, compound

HRID 1183793Notes

Reaction equation

HRID 1183793 reaction equation
[CH3:1][C:2]1[C:10]2[S:9][NH:8][C:7](=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.CN(C)C=O.S(Cl)([Cl:19])=O>C1(C)C=CC=CC=1>[Cl:19][C:7]1[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[C:10]=2[S:9][N:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 19076692HCID 19076692, compound

Product 1

HCID 57879640HCID 57879640, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 1 L four-neck flask equipped with a stirrer, a thermometer and a condenser tube was charged with 82.6 g (0.5 mol) of 7-methyl-1,2-benzisothiazol-3-one, 80.4 g (1.1 mol) of N,N-dimethylformamide and 200.0 g of toluene. While stirring, 83.3 g (0.7 mol) of thionyl chloride was added dropwise thereto at 70° to 80° 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 distillated under reduced pressure of 0.40 kPa at 110° C. to give 81.7 g (0.45 mol) of 3-chloro-7-methyl-1,2-benzisothiazole. The yield based on 7-methyl-1,2-benzisothiazol-3-one was 89%.

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 distillated under reduced pressure of 0.40 kPa at 110° C.

Sources & evidence

ORD record
ord-add80d5cd62f4eb9ae0b55fbc71c6407
Source dataset
uspto-grants-2014_03
Patent number
US08664404B2

Reaction notes

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