Thiophenol → HCID 54347543, compound

HRID 1253342Notes

Reaction equation

HRID 1253342 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[S:13][CH:14]=[C:15]([C:17](=[C:21](Cl)[CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[C:18]([OH:20])=[O:19])[N:16]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(S)C=CC=CC=1.C(N(CC)CC)C>O1CCCC1>[CH2:1]([O:8][C:9]([NH:11][C:12]1[S:13][CH:14]=[C:15]([C:17](=[CH:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[O:26])[C:18]([OH:20])=[O:19])[N:16]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 53884697HCID 53884697, compound

Product 1

HCID 54347543HCID 54347543, compoundYield 118.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of diester (4) (3.03 g) in tetrahydrofuran (30 ml) are added benzenethiol (0.70 ml) and triethylamine (0.79 ml). The mixture is stirred at room temperature for 3.5 hours, concentrated, and purified by silica gel chromatography (eluting with benzene-ethyl acetate (9:1 to 8:2) mixture) to give phenylthiopropionate (5) (3.36 g). Yield: 92%.

Workup

  1. concentrationconcentrated
  2. custompurified by silica gel chromatography (eluting with benzene-ethyl acetate (9:1 to 8:2) mixture)

Sources & evidence

ORD record
ord-bae36351ec224663905374c46eae0956
Source dataset
uspto-grants-1988_05
Patent number
US04748170

Reaction notes

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