Acetyl chloride → HCID 14855876, compound

HRID 1709643Notes

Reaction equation

HRID 1709643 reaction equation
[F:1][C:2]([F:17])=[CH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([NH:15][NH2:16])=[O:14].C(N(CC)CC)C.[C:25](Cl)(=[O:27])[CH3:26]>C(OCC)C>[C:25]([NH:16][NH:15][C:13](=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[C:2]([F:17])[F:1])(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 14855875HCID 14855875, compound

Product 1

HCID 14855876HCID 14855876, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 0.5 gram (0.002 mole) of 12,12-difluoro-11-dodecenoic acid hydrazide and 0.3 gram (0.003 mole) of triethylamine in 20 ml of diethyl ether was stirred, and 0.2 gram (0.003 mole) of acetyl chloride was added. The reaction mixture was stirred at ambient temperature for 30 minutes and was filtered. The filtrate was in turn washed with aqueous 10% hydrochloric acid, aqueous 10% sodium hydroxide, and an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure yielding 0.4 gram of 12,12-difluoro-11-dodecenoic acid 2-acetylhydrazide. The nmr spectrum was consistent with the proposed structure.

Workup

  1. filtrationwas filtered
  2. washwashed with aqueous 10% hydrochloric acid, aqueous 10% sodium hydroxide
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-88c9b1f052df47c9b5caf19236da8fd8
Source dataset
uspto-grants-1990_08
Patent number
US04950666

Reaction notes

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