Sodium methanethiolate → HCID 67896175, compound

HRID 1196681Notes

Reaction equation

HRID 1196681 reaction equation
Br[CH:2]1[C:8]2[C:9]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)=[N:10][O:11][C:7]=2[CH2:6][CH:5]([C:19]([O:21][CH3:22])=[O:20])[CH2:4][CH2:3]1.[CH3:23][S-:24].[Na+]>CN(C)C=O>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]2[C:8]3[C@H:2]([S:24][CH3:23])[CH2:3][CH2:4][C@H:5]([C:19]([O:21][CH3:22])=[O:20])[CH2:6][C:7]=3[O:11][N:10]=2)=[CH:13][CH:14]=1.[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]2[C:8]3[C@H:2]([S:24][CH3:23])[CH2:3][CH2:4][C@@H:5]([C:19]([O:21][CH3:22])=[O:20])[CH2:6][C:7]=3[O:11][N:10]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 19899058HCID 19899058, compound

Product 2

HCID 67896175HCID 67896175, compoundHCID 67896359HCID 67896359, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.5 g (1.3 mmol) of a cis/trans mixture of methyl 4-bromo-3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4H-cyclohept[d]isoxazole-7-carboxylate (prepared as described in Example 9) in 5 ml of dry dimethylformamide was stirred, cooled in ice and treated with 0.15 g (2.1 mmol) of sodium methanethiolate. The mixture was stirred at room temperature for 24 hours and then evaporated. The residue was partitioned between water and dichloromethane and the organic phase was dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel using dichloromethane for the elution and there were obtained 0.028 g of methyl cis-3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4-methylthio-4H-cyclohept[d]isoxazole-7-carboxylate of melting point 110°-112° C. and 0.041 g of methyl trans-3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4-methylthio-4H-cyclohept[d]isoxazole-7-carboxylate of melting point 127°-128° C.

Workup

  1. temperaturecooled in ice
  2. customevaporated
  3. customThe residue was partitioned between water and dichloromethane
  4. dry with materialthe organic phase was dried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. washfor the elution

Sources & evidence

ORD record
ord-1ca4da3d612e465cb8c7df09f8494547
Source dataset
uspto-grants-1992_05
Patent number
US05114960

Reaction notes

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