Methanesulfonyl chloride → HCID 54542349, compound

HRID 1576971Notes

Reaction equation

HRID 1576971 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([Cl:9])=[N:7][OH:8])=[CH:4][CH:3]=1.[CH3:12][S:13](Cl)(=[O:15])=[O:14]>C1C=CC=CC=1>[CH3:12][S:13]([O:8][N:7]=[C:6]([Cl:9])[C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:11][CH:10]=1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 3303868HCID 3303868, compound

Product 1

HCID 54542349HCID 54542349, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In a second synthesis, 10 g of 4-methylbenzohydroximoyl chloride, 6.7 g of methanesulfonyl chloride, and 160 ml of benzene were mixed in a 250-ml, three-necked, round-bottomed flask equipped with a stirrer, thermometer, and drying tube. Triethylamine (8.8 g) was added dropwise during 6 minutes at 5°-10°, and the mixture was stirred at that temperature for 1 hour. The reaction mixture was filtered, the solid was washed with benzene, the washes and filtrate were combined and concentrated, and the concentrate was recrystallized from ethanol to give 9 g of N-(methanesulfonyloxy)-4-methylbenzimidoyl chloride, m.p. 100°-102°. The ir spectrum was consistent with the assigned structure.

Workup

  1. additionwere mixed in a 250-ml
  2. customthree-necked, round-bottomed flask equipped with a stirrer
  3. customthermometer, and drying tube
  4. additionTriethylamine (8.8 g) was added dropwise during 6 minutes at 5°-10°
  5. filtrationThe reaction mixture was filtered
  6. washthe solid was washed with benzene
  7. concentrationconcentrated
  8. customthe concentrate was recrystallized from ethanol

Sources & evidence

ORD record
ord-44cf84dc2d594cc39b56c1b42bd0fd1e
Source dataset
uspto-grants-1976_09
Patent number
US03983246

Reaction notes

Loading…