Trichloromethanethiol → CF(NO2)2CH2OSCCl3

HRID 247235

Reaction equation

HRID 247235 reaction equation
[Cl:1][C:2]([SH:5])([Cl:4])[Cl:3].[F:6][C:7]([N+:13]([O-:15])=[O:14])([N+:10]([O-:12])=[O:11])[CH2:8][OH:9].[OH-].[Na+]>C(Cl)Cl.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:7]([CH2:8][O:9][S:5][C:2]([Cl:4])([Cl:3])[Cl:1])([N+:13]([O-:15])=[O:14])([N+:10]([O-:12])=[O:11])[F:6]

Participants

7

Reactant 3

HCID 6390TrichloromethanethiolHCID 14798Sodium HydroxideHCID 28189Ethanol, 2-fluoro-2,2-dinitro-

Product 1

HCID 13149209CF(NO2)2CH2OSCCl3Yield 90.1%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Perchloromethylmercaptan (5.6 g, 0.03 mol) and 2-fluoro-2,2-dinitroethanol (5.0 g, 0.033 mol) in 30 ml of methylene chloride was combined with 0.3 g of tetrabutyl ammonium chloride in 20 ml of water and the vigorously stirred mixture was cooled in an ice-salt bath. A solution obtained by diluting 2.6 g of 50 percent aqueous sodium hydroxide with 3 ml of water was added dropwise keeping the temperature at 0° C. Separation of the methylene chloride layer and removal of the solvent gave 8.2 g of an oil which was extracted with 2×40 ml of hexane. The combined extracts were passed through a silica gel 60 pad and the pad was washed with benzene. Removal of solvent gave 5.9 g (65 percent) of an oil which was essentially pure by TLC and GLC analysis; H-NMR (CDCl3): δ 5.37 (d); mass spectrum (C.I.): m/e 304, 302, 267, 269.

Workup

  1. temperaturethe vigorously stirred mixture was cooled in an ice-salt bath
  2. customA solution obtained
  3. additionwas added dropwise
  4. customat 0° C
  5. customSeparation of the methylene chloride layer and removal of the solvent

Sources & evidence

ORD record
ord-e0788e2bcfe64239abd283e592cff4ee
Source dataset
uspto-grants-1987_11
Patent number
US04705899

Linked notes

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