Triethylamine → HCID 352955, compound

HRID 1576976Notes

Reaction equation

HRID 1576976 reaction equation
[C:1]([Cl:10])(=[N:8][OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>CCOCC>[CH3:18][S:19]([O:9][N:8]=[C:1]([Cl:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2756315N-hydroxybenzenecarboximidoyl chloride

Product 1

HCID 352955HCID 352955, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The 9.4 g of recovered benzohydroximoyl chloride was dissolved in 100 ml of anhydrous ether and the solution was cooled to -20°. To the cold solution was rapidly added 12.3 g of triethylamine. To this mixture was slowly added (during 45 minutes) a solution of 6.95 g of methanesulfonyl chloride in 50 ml of anhydrous ether. The mixture was stirred at -30° for 1 hour, then at ambient temperature for about 16 hours. The mixture was filtered and the filtrate was conconcentrated under reduced pressure to give a yellow solid. The solid was recrystallized from a benzene-hexane mixture to give 5.2 g of N-(methanesulfonyloxy)benzimidoyl chloride, m.p. 106°-108°.

Workup

  1. temperaturethe solution was cooled to -20°
  2. waitat ambient temperature for about 16 hours
  3. filtrationThe mixture was filtered
  4. customto give a yellow solid
  5. customThe solid was recrystallized from a benzene-hexane mixture

Sources & evidence

ORD record
ord-d652e83444654308bede2657cf553512
Source dataset
uspto-grants-1976_09
Patent number
US03983246

Reaction notes

Loading…