Dichloromethane → N-Methyl-N-(2-methyl-1,3-dichloro-2-propanesulfenyl)carbamoyl fluoride

HRID 1763396Notes

Reaction equation

HRID 1763396 reaction equation
[CH2:1]([Cl:5])[C:2](=[CH2:4])[CH3:3].[CH3:6][N:7]([S:11]Cl)[C:8]([F:10])=[O:9].C(Cl)[Cl:14]>>[CH3:6][N:7]([S:11][C:2]([CH3:3])([CH2:4][Cl:14])[CH2:1][Cl:5])[C:8]([F:10])=[O:9]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 112413-Chloro-2-methyl-1-propeneHCID 12922862N-chlorothio(methyl)carbamoyl fluoride

Product 1

HCID 54204012N-Methyl-N-(2-methyl-1,3-dichloro-2-propanesulfenyl)carbamoyl fluoride

Procedure

To a solution of 1.35g of methallyl chloride in 25 ml of methylene chloride was added 2.15g of N-methyl-N-chlorosulfenyl carbamoyl fluoride. The solution was heated to reflux for 45 min. and concentrated to 1.68g of pale yellow oil. Infra-red (neat) 5.57 (C=O), 6.9, 7.0, 7.26, 7.65, 8.45, 9.15, 10.42, 12.3, 13.3 and 14.1μ. NMR (CDCl3) δ 1.39 (s), 3H; 3.36 (d), J = 1.0 HZ, 3H, 3.92 (s), 4H.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 45 min.
  3. concentrationconcentrated to 1.68g of pale yellow oil

Sources & evidence

ORD record
ord-bc0eb5e9661b4c3083fb5bf1b04aaab0
Source dataset
uspto-grants-1978_09
Patent number
US04111989

Reaction notes

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