Methanesulfonyl chloride → HCID 54213645, compound

HRID 1576987Notes

Reaction equation

HRID 1576987 reaction equation
[CH:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([Cl:11])=[N:9][OH:10])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH3:14][S:15](Cl)(=[O:17])=[O:16]>C1C=CC=CC=1.C(N(CC)CC)C>[CH3:14][S:15]([O:10][N:9]=[C:8]([Cl:11])[C:7]1[CH:12]=[CH:13][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=1)(=[O:17])=[O:16]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 71391085N-Hydroxy-4-(propan-2-yl)benzene-1-carboximidoyl chloride

Product 1

HCID 54213645HCID 54213645, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8471TriethylamineSolvent

Procedure

Into a solution of 6.7 g of 4-isopropylbenzohydroximoyl chloride in 175 ml of benzene was added in one portion 5.2 g of triethylamine. To this solution was added dropwise during 15 minutes (mildly exothermic reaction) 4.0 g of methanesulfonyl chloride. The mixture was stirred for 30 minutes and filtered. The filtrate was concentrated and the residue recrystallized twice from ethanol to give 8.1 g of N-(methanesulfonyloxy)-4-isopropylbenzimidoyl chloride, m.p. 79.5°-82°. The ir spectrum was consistent with the assigned structure.

Workup

  1. additionTo this solution was added dropwise during 15 minutes (
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customthe residue recrystallized twice from ethanol

Sources & evidence

ORD record
ord-caf307f749594332a2ba9bdabf04f5df
Source dataset
uspto-grants-1976_09
Patent number
US03983246

Reaction notes

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