Ammonium Chloride → HCID 86749069, compound

HRID 2211016Notes

Reaction equation

HRID 2211016 reaction equation
[SH:1][C:2]([C@H:5]1[O:10][C:8](=[O:9])[C@@H:7]([CH2:11][SH:12])[CH2:6]1)([CH3:4])[CH3:3].[Cl-].[NH4+]>C(Cl)Cl.C(N(CC)CC)C.C(Cl)(=O)C>[C:8]([S:1][C:2]([C@H:5]1[O:10][C:8](=[O:9])[C@@H:7]([CH2:11][S:12][C:5](=[O:10])[CH3:2])[CH2:6]1)([CH3:4])[CH3:3])(=[O:9])[CH3:7]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86747635HCID 86747635, compound

Product 1

HCID 86749069HCID 86749069, compoundYield 185.3%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6367Acetyl chlorideSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred solution of cis-4-(1-mercapto-1-methylethyl)-2-mercaptomethyl-4-butanolide (compound No.9-3, 0.102 g) in methylene chloride (3 ml), triethylamine (0.20 ml) and acetyl chloride (0.10 ml) were added and stirred for 30 minutes under nitrogen atmosphere and ice-cooling. The mixture was poured into saturated aqueous ammonium chloride solution (30 ml) and extracted with ether. The organic layer was washed with saturated aqueous ammonium chloride solution and saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The oily residue was purified by silica gel column chromatography to give 0.133 g (93%) of the titled compound.

Workup

  1. temperatureice-cooling
  2. extractionextracted with ether
  3. washThe organic layer was washed with saturated aqueous ammonium chloride solution and saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe oily residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d8b664b75889486aa83c4be39f438129
Source dataset
uspto-grants-1995_10
Patent number
US05461158

Reaction notes

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