Methanethiol → HCID 22621111, compound

HRID 610756Notes

Reaction equation

HRID 610756 reaction equation
[CH3:1][SH:2].[Cl:3][C:4]1[C:5]([N:16]([CH2:21][CH3:22])[S:17]([CH3:20])(=[O:19])=[O:18])=[C:6]([CH:12]=[CH:13][C:14]=1F)[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:3][C:4]1[C:5]([N:16]([CH2:21][CH3:22])[S:17]([CH3:20])(=[O:19])=[O:18])=[C:6]([CH:12]=[CH:13][C:14]=1[S:2][CH3:1])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 4

HCID 878MethanethiolHCID 962WaterHCID 11430Potassium CarbonateHCID 22620998HCID 22620998, compound

Product 1

HCID 22621111HCID 22621111, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution of methanethiol (4 ml) in dry DMF was added to a mixture of ethyl 3-chloro-2-(N-ethyl-N-methylsulphonylamino)-4-fluorobenzoate (7.4 g) and anhydrous potassium carbonate (4.71 g) in DMF at -40° C. The mixture was maintained at -10° C. for 1 hour, then warmed to ambient temperature over 2.5 hours. Water was added and the mixture extracted with ether, washed with brine solution then water, dried (anhydrous magnesium sulphate) and the solvent evaporated to give ethyl 3-chloro-2-(N-ethyl-N-methylsulphonylamino)-4-(methylthio)benzoate (8.3 g) as a white powder, m.p. 109-110.5° C.

Workup

  1. temperaturewarmed to ambient temperature over 2.5 hours
  2. extractionthe mixture extracted with ether
  3. washwashed with brine solution
  4. dry with materialwater, dried (anhydrous magnesium sulphate)
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-1b9f7230c8ea4220b5df3a1a0f40da9a
Source dataset
uspto-grants-1999_12
Patent number
US05998653

Reaction notes

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