Dichloroacetyl chloride → HCID 178524651, compound

HRID 328063Notes

Reaction equation

HRID 328063 reaction equation
[NH2:1][CH:2]1[C:19](=[O:20])[N:4]2[C:5]([C:16]([OH:18])=[O:17])=[C:6]([CH2:9][S:10][C:11]3[NH:15][CH:14]=[N:13][N:12]=3)[CH2:7][S:8][C@H:3]12.C[Si](C([Si](C)(C)C)C(N)=O)(C)C.[Cl:33][CH:34]([Cl:38])[C:35](Cl)=[O:36]>C(Cl)Cl>[Cl:33][CH:34]([Cl:38])[C:35]([NH:1][CH:2]1[C:19](=[O:20])[N:4]2[C:5]([C:16]([OH:18])=[O:17])=[C:6]([CH2:9][S:10][C:11]3[NH:15][CH:14]=[N:13][N:12]=3)[CH2:7][S:8][C@H:3]12)=[O:36]

Participants

5

Reactant 3

HCID 6593Dichloroacetyl chlorideHCID 11708267BistrimethylsilylacetamidHCID 178508105HCID 178508105, compound

Product 1

HCID 178524651HCID 178524651, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

7-Amino-3-(4H-1,2,4-triazol-3-ylthiomethyl)-3-cephem-4-carboxylic acid (3.13 g) was suspended in dried methylene chloride (30 ml) and bis(trimethylsilyl)acetamide (6.10 g) was added to the suspension to give a solution. A solution of dichloroacetyl chloride (1.62 g) in dried methylene chloride (20 ml) was added slowly to the solution at -20° C. The mixture was stirred at the same temperature for 30 minutes and then allowed to stand at room temperature. Methylene chloride was distilled off from the reaction mixture under reduced pressure. To the residue was added ice water and the aqueous solution was adjusted to pH 8 with 5% aqueous sodium bicarbonate, washed with ethyl acetate and then filtered. The filtrate was adjusted to pH 2 with 10% hydrochloric acid and extracted with ethyl acetate (50 ml) three times. These extracts were put together, washed with water twice and with saturated aqueous sodium chloride and dried over magnesium sulfate. Ethyl acetate was distilled off from the solution under reduced pressure. To the residue was added ether and the mixture was stirred. Precipitates were collected by filtration and dried to give 7-dichloroacetamido-3-(4H-1,2,4-triazol-3-ylthiomethyl)-3-cephem-4-carboxylic acid (2.95 g).

Workup

  1. customto give a solution
  2. customto stand at room temperature
  3. distillationMethylene chloride was distilled off from the reaction mixture under reduced pressure
  4. additionTo the residue was added ice water
  5. washwashed with ethyl acetate
  6. filtrationfiltered
  7. extractionextracted with ethyl acetate (50 ml) three times
  8. washwashed with water twice
  9. dry with materialwith saturated aqueous sodium chloride and dried over magnesium sulfate
  10. distillationEthyl acetate was distilled off from the solution under reduced pressure
  11. additionTo the residue was added ether
  12. stirringthe mixture was stirred
  13. customPrecipitates
  14. filtrationwere collected by filtration
  15. customdried

Sources & evidence

ORD record
ord-4d5e41a031f34d62a5dff1424ee6afa0
Source dataset
uspto-grants-1977_04
Patent number
US04016160

Reaction notes

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