Methanethiol → HCID 22621111, compound

HRID 841166Notes

Reaction equation

HRID 841166 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-be686ea61ef74164abe3785ceb5304f0
Source dataset
uspto-grants-2002_04
Patent number
US06369270B1

Reaction notes

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