Potassium Hydroxide → S-methyl N-[N'-methyl-N'-(dimethylaminosulfenyl)-carbamoyloxy]thioacetimidate

HRID 1447117Notes

Reaction equation

HRID 1447117 reaction equation
[OH-].[K+].[CH3:3][SH-:4][C:5](=[N:7][OH:8])[CH3:6].[CH3:9][N:10]([S:14][N:15]([CH3:17])[CH3:16])[C:11](F)=[O:12]>C1CC2OCCOCCOC3C(OCCOCCOC2CC1)CCCC3.C1C=CC=CC=1>[CH3:9][N:10]([S:14][N:15]([CH3:17])[CH3:16])[C:11]([O:8][N:7]=[C:5]([S:4][CH3:3])[CH3:6])=[O:12]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 12799216N-methyl-N-(dimethylaminosulfenyl)carbamoyl fluorideHCID 178504139HCID 178504139, compound

Product 1

HCID 54514859S-methyl N-[N'-methyl-N'-(dimethylaminosulfenyl)-carbamoyloxy]thioacetimidateYield 77.4%

Reagents, catalysts & solvents 2

HCID 85955Dicyclohexano-18-crown-6CatalystHCID 241BenzeneSolvent

Procedure

Powdered potassium hydroxide (3.3 g), 5.2 g of S-methyl-N-hydroxythioacetimidate, 0.1 g dicyclohexyl-18-crown-6, and 200 ml of benzene were stirred at room temperature for 0.5 hr. Then 8.0 g of N-methyl-N-(dimethylaminosulfenyl)carbamoyl fluoride was added slowly at 28° C. The reaction temperature was held at 28°-32° C. with external cooling. The mixture was stirred for 1 hr., and then was washed with water until neutral. After drying (MgSO4), the solution was concentrated in vacuo, and the residue was recrystallized from diisopropyl ether to give 9.0 g (76 percent yield) of S-methyl N-[N'-methyl-N'-(dimethylaminosulfenyl)carbamoyloxy]Thioacetimidate, m.p. 68°-70° C.

Workup

  1. customwas held at 28°-32° C. with external cooling
  2. wash, and then was washed with water until neutral
  3. dry with materialAfter drying (MgSO4)
  4. concentrationthe solution was concentrated in vacuo
  5. customthe residue was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-8fffadb1e6ee4033ba0a4cdf1a1b0fd3
Source dataset
uspto-grants-1982_02
Patent number
US04315928

Reaction notes

Loading…