Thiophenol → S-Phenyl 2-(2-naphthyl)ethanethioate

HRID 1184683

Reaction equation

HRID 1184683 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12](Cl)=[O:13].C(N(CC)CC)C.[C:22]1([SH:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCCC(C)C.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12](=[O:13])[S:28][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 8471TriethylamineHCID 5881152-(2-Naphthyl)acetyl chlorideHCID 21882781Isohexane ethyl acetate

Product 1

HCID 86656471S-Phenyl 2-(2-naphthyl)ethanethioateYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

2-(2-Naphthyl)acetyl chloride (308 mg, 1.5 mmol) in 4.5 mL toluene was added to a solution of triethylamine (0.21 mL, 1.5 mmol) and thiophenol (153 μL, 1.5 mmol) in 3 mL toluene. Reaction monitoring was accomplished by TLC: iso-hexane/ethyl acetate 25:1, Rf=0.33. Workup yielded 376 mg (90%) S-phenyl 2-(2-naphthyl)ethanethioate 9 as yellow solid.

Workup

  1. customReaction monitoring

Sources & evidence

ORD record
ord-942f4611a8024f368e75d857f8d7bdc4
Source dataset
uspto-grants-2014_03
Patent number
US08669283B2

Linked notes

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