Thiophenol → HCID 3249365, compound

HRID 389348Notes

Reaction equation

HRID 389348 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:9]([O:11][CH:12]([Cl:14])[CH3:13])=[O:10].C(N(CC)CC)C>C(Cl)Cl>[C:9](=[O:10])([S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[O:11][CH:12]([Cl:14])[CH3:13]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 5213051-Chloroethyl chloroformate

Product 1

HCID 3249365HCID 3249365, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of benzenethiol (50 g, 450 mmol) and 1-chloroethyl chloroformate (65 g, 450 mmol) in CH2Cl2 (300 mL) was cooled to 0-4° C. in an ice-water bath. To the mixture was added a solution of triethylamine (450 mmol) in dichloromethane (200 mL) dropwise over 30 min. The reaction was removed from the ice bath and stirred at ambient temperature for 12 h. The reaction was washed with water (3×500 mL), the organic phase was separated, dried over anhydrous magnesium sulfate and concentrated in vacuo to afford the product as a pale yellow liquid (96 g, 98.5%). 1H NMR (CDCl3, 400 MHz): δ 1.82 (d, 3H), 6.6 (q, 1H), 7.2-7.4 (m, 5H).

Workup

  1. customThe reaction was removed from the ice bath
  2. washThe reaction was washed with water (3×500 mL)
  3. customthe organic phase was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0b6b5ae3d8e941868e520da55b697227
Source dataset
uspto-grants-2013_02
Patent number
US08378137B2

Reaction notes

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