Triethylamine → N-(methanesulfonyloxy)-4-chlorobenzimidoyl chloride

HRID 1576974Notes

Reaction equation

HRID 1576974 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([Cl:9])=[N:7][OH:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(OCC)C>[CH3:19][S:20]([O:8][N:7]=[C:6]([Cl:9])[C:5]1[CH:10]=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 27555434-chloro-N-hydroxybenzene-1-carbonimidoyl chloride

Product 1

HCID 54492654N-(methanesulfonyloxy)-4-chlorobenzimidoyl chlorideYield 56.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 9.8 g of 4-chlorobenzohydroximoyl chloride in 300 ml of diethyl ether was chilled to 5°. To it was quickly added 10.4 g of triethylamine and, after 5 minutes, a solution of 6.1 g of methanesulfonyl chloride in 30 ml of diethyl ether was added dropwise during 30 minutes. The mixture was stirred for 1 hour at 0°-5°, followed by 1 hour at ambient temperature. The mixture was again cooled to 5°, then filtered, and the filter cake was washed with cold ether. The filtrate and washes were combined and the other evaporated under reduced pressure to leave a yellow oil. The oil was crystallized from a mixture of benzene and hexane to give 7.8 g of N-(methanesulfonyloxy)-4-chlorobenzimidoyl chloride, m.p. 80°-82°.

Workup

  1. waitfollowed by 1 hour at ambient temperature
  2. temperatureThe mixture was again cooled to 5°
  3. filtrationfiltered
  4. washthe filter cake was washed with cold ether
  5. customthe other evaporated under reduced pressure
  6. customto leave a yellow oil
  7. customThe oil was crystallized from a mixture of benzene and hexane

Sources & evidence

ORD record
ord-2c86fd00ffd94d2280bdf6633ea39393
Source dataset
uspto-grants-1976_09
Patent number
US03983246

Reaction notes

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