Sodium methanethiolate → HCID 21112946, compound

HRID 1767200Notes

Reaction equation

HRID 1767200 reaction equation
[CH3:1][S-:2].[Na+].C([O:6][C:7](=[O:29])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH2:18][CH2:17][CH2:16][C:15]=2[C:19]2[CH:24]=[C:23](SC)[CH:22]=[CH:21][C:20]=2[O:27]C)[CH:9]=1)C.C([O:32]CC)C.[OH2:35]>CN(C)C=O>[CH3:1][S:2]([C:23]1[CH:22]=[CH:21][C:20]([OH:27])=[C:19]([C:15]2[CH2:16][CH2:17][CH2:18][C:14]=2[C:10]2[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=2)[C:7]([OH:6])=[O:29])[CH:24]=1)(=[O:32])=[O:35]

Participants

5

Reactant 3

HCID 4378561Sodium methanethiolateHCID 21584184Diethylether waterHCID 58887619HCID 58887619, compound

Product 1

HCID 21112946HCID 21112946, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of sodium methanethiolate (700 mg, 10 mmol) and (3-{2-[5-methylsulfanyl-2-(methoxy-)-phenyl]-cyclopent-1-enyl}-benzoic acid ethyl ester (720 mg, 1.96 mmol) in dimethylformamide (15 ml) was stirred and heated at 120° C. under nitrogen for 5 hours. After cooling the mixture was diluted with diethyl ether/water and the aqueous phase separated and acidified with hydrochloric acid then extracted with diethyl ether. The organic phase was dried (MgSO4), evaporated to dryness and the residue triturated with diethyl ether/iso-hexane to yield the title compound as a white solid, (437 mg, 68%).

Workup

  1. temperatureAfter cooling the mixture
  2. customthe aqueous phase separated
  3. extractionthen extracted with diethyl ether
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated to dryness
  6. customthe residue triturated with diethyl ether/iso-hexane

Sources & evidence

ORD record
ord-e4eb4b7fffef40db81084b53083839dc
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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