Acetyl chloride → p-Acetamidophenyl methyl disulfide

HRID 1024587

Reaction equation

HRID 1024587 reaction equation
[CH3:1][S:2][S:3][C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:18](Cl)(=[O:20])[CH3:19].C(OCC)(=O)C>C(Cl)Cl>[CH3:1][S:2][S:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:18](=[O:20])[CH3:19])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 25001884p-Aminophenyl methyl disulfide

Product 1

HCID 24997137p-Acetamidophenyl methyl disulfide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 39a (50 mg, 0.3 mmol) in dry CH2Cl2 (3 ml) was added triethylamine (127 μL, 0.9 mmol, 3 eq.), followed by acetyl chloride (32 μL, 0.45 mmol). The reaction was stirred at RT for 1 hr., then was diluted with dichloromethane, washed with water, then 5% aq. HCl, then 5% aq. NaHCO3. Dried over MgSO4, then concentrated in vacuo to give a yellow oil which solidified on standing. Chromotography (1:1 petroleum ether:ethyl acetate) gave 18 mg (29%) as a light brown solid. 1H NMR (400 MHz, CDCl3): δ 7.47 (s, 4H); 2.41 (s, 3H); 2.16 (s, 3H).

Workup

  1. washwashed with water
  2. dry with materialDried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customto give a yellow oil which

Sources & evidence

ORD record
ord-02865d9f5c6c4fc39296565f96c43ef5
Source dataset
uspto-grants-2014_05
Patent number
US08722937B2

Linked notes

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