Trichloromethanesulfenyl chloride → HCID 13193083, compound

HRID 1919281Notes

Reaction equation

HRID 1919281 reaction equation
[CH3:1][C:2]([C:5]([NH2:7])=[NH:6])([CH3:4])[CH3:3].Cl.[Cl:9][C:10](Cl)(Cl)[S:11]Cl.[OH-].[Na+]>ClCCl.O>[C:2]([C:5]1[N:7]=[C:10]([Cl:9])[S:11][N:6]=1)([CH3:4])([CH3:3])[CH3:1]

Participants

6

Reactant 3

HCID 11666Trichloromethanesulfenyl chlorideHCID 14798Sodium HydroxideHCID 2781880Propanimidamide, 2,2-dimethyl-, hydrochloride (1:1)

Product 1

HCID 13193083HCID 13193083, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

6.83 g (50.00 mmol) of tert-butylcarbamidine hydrochloride are dissolved in 60 ml of dichloromethane and treated with 8.37 g (45.00 mmol) of trichloromethanesulphenyl chloride, before the reaction mixture is cooled to −15° C. A solution of 10.00 g (250 mmol) of sodium hydroxide in 20 ml of water is added dropwise and the mixture obtained is stirred at AT for 3 h. After adding 50 ml of dichloromethane, extracting three times with water and drying the combined organic phases over MgSO4, the solvent is evaporated under vacuum. (5.81 g, 90% purity, 60% yield, log P (pH 2.3)=3.44).

Workup

  1. customthe mixture obtained
  2. extractionextracting three times with water
  3. dry with materialdrying the combined organic phases over MgSO4
  4. customthe solvent is evaporated under vacuum

Sources & evidence

ORD record
ord-6ecfca2cb2f4480d83dd78ee9f3ae4c0
Source dataset
uspto-grants-2012_05
Patent number
US08168567B2

Reaction notes

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