Ethanethiol → 2-Chloro-6-(trimethylsilyl)benzenecarbothioic acid, S-ethyl ester

HRID 1458064Notes

Reaction equation

HRID 1458064 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Si:11]([CH3:14])([CH3:13])[CH3:12])[C:3]=1[C:4](Cl)=[O:5].[CH2:15]([SH:17])[CH3:16]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Si:11]([CH3:14])([CH3:13])[CH3:12])[C:3]=1[C:4](=[O:5])[S:17][CH2:15][CH3:16]

Participants

5

Reactant 2

HCID 6343EthanethiolHCID 151835572-Chloro-6-(trimethylsilyl)benzoyl chloride

Product 1

HCID 861641552-Chloro-6-(trimethylsilyl)benzenecarbothioic acid, S-ethyl esterYield 61%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The compound of Example b (1.48 g, 0.006 mol), CH2Cl2 (50 mL), ethanethiol (0.44 g, 0.007 mol), and 4-(N,N-dimethylamino)pyridine (0.86 g, 0.007 mol) were allowed to stir at RT overnight. The mixture was washed with 10% HCl and three times with water, dried (MgSO4), and concentrated. The crude product was purified by RC, eluting with 1:3 ethyl acetate/hexanes. The title compound was obtained as a clear oil in 61% yield.

Workup

  1. washThe mixture was washed with 10% HCl and three times with water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe crude product was purified by RC
  5. washeluting with 1:3 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-330ba0bf4e9c4418bb983d95fb973741
Source dataset
uspto-grants-1998_12
Patent number
US05849723

Reaction notes

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