Benzene → S-methyl N-[N'-methyl-N'-(diisopropylaminosulfenyl)carbamoyloxy]thioacetimidate

HRID 1447121Notes

Reaction equation

HRID 1447121 reaction equation
[OH-].[K+].[CH3:3][SH-:4][C:5](=[N:7][OH:8])[CH3:6].C1C=CC=CC=1.[CH3:15][N:16]([S:20][N:21]([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])[C:17](F)=[O:18]>C1CC2OCCOCCOC3C(OCCOCCOC2CC1)CCCC3.O>[CH3:15][N:16]([S:20][N:21]([CH:22]([CH3:24])[CH3:23])[CH:25]([CH3:26])[CH3:27])[C:17]([O:8][N:7]=[C:5]([S:4][CH3:3])[CH3:6])=[O:18]

Participants

7

Reactant 4

HCID 241BenzeneHCID 14797Potassium HydroxideHCID 20551373N-methyl-N-(diisopropylaminosulfenyl)carbamoyl fluorideHCID 178504139HCID 178504139, compound

Product 1

HCID 54073397S-methyl N-[N'-methyl-N'-(diisopropylaminosulfenyl)carbamoyloxy]thioacetimidateYield 67.3%

Reagents, catalysts & solvents 2

HCID 85955Dicyclohexano-18-crown-6CatalystHCID 962WaterSolvent

Procedure

Powdered potassium hydroxide (2.5 g), 4.7 g. 10.045 mole) of S-methyl-N-hydroxythioacetimidate, 0.11 g dicyclohexyl-18-crown-6, and benzene (200 mol) were combined and stirred 0.5 hr. at room temperature. Then 9.4 g (0.045 mole) of N-methyl-N-(diisopropylaminosulfenyl)carbamoyl fluoride were added. The mixure was stirred at room temperature for 1 hr., and then was water washed four times, dried (MgSO4), and the benzene solvent was removed under vacuum. The residue was recrystallized from diisopropyl ether to give 9 g (67.3 percent yield) of S-methyl N-[N'-methyl-N'-(diisopropylaminosulfenyl)carbamoyloxy]thioacetimidate, m.p. 79°-80° C.

Workup

  1. customat room temperature
  2. stirringThe mixure was stirred at room temperature for 1 hr
  3. washwashed four times
  4. dry with materialdried (MgSO4)
  5. customthe benzene solvent was removed under vacuum
  6. customThe residue was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-e978ca652bec4673983b17d8c5da3c44
Source dataset
uspto-grants-1982_02
Patent number
US04315928

Reaction notes

Loading…