Chloroacetyl chloride → 3,4-dichloro-N'-(2-chloroacetyl)benzohydrazide

HRID 334522Notes

Reaction equation

HRID 334522 reaction equation
Cl[C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[C:4]([NH:6][NH2:7])=[O:5].[Cl:13]Cl.CCN(C(C)C)C(C)C.[Cl:24][CH2:25][C:26](Cl)=[O:27]>>[Cl:13][C:11]1[CH:2]=[C:3]([CH:8]=[CH:9][C:10]=1[Cl:12])[C:4]([NH:6][NH:7][C:26](=[O:27])[CH2:25][Cl:24])=[O:5]

Participants

5

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 1385962,4-Dichlorobenzohydrazide

Product 1

HCID 674793863,4-dichloro-N'-(2-chloroacetyl)benzohydrazideYield 50%

Procedure

To a solution of compound 8 (370 mg, 0.934 mmol) in 5 ml of CH2 Cl2 was added DIPEA (180 mg, 1.4 mmol) at 0° C. and stirred for 10 minutes. Then chloroacetyl chloride (116 mg, 1.02 mmol) was added slowly at the same temperature and the mixture was warmed to ambient temperature and stirred overnight. Solvent was removed to give the crude compound which was used in the next step without any further purification. The crude compound was heated to reflux in toluene (25 ml) using Dean-Stark for 12 hours. Then the toluene was distilled and the crude material purified by column chromatography using EtOAc:Hexane (45:55) as an eluent to afford compound 9 as a pale yellow gummy material (212 mg). Yield: 50%.

Workup

  1. stirringstirred overnight
  2. customSolvent was removed
  3. customto give the crude compound which
  4. customwas used in the next step without any further purification
  5. temperatureThe crude compound was heated
  6. temperatureto reflux in toluene (25 ml)
  7. customfor 12 hours
  8. distillationThen the toluene was distilled
  9. customthe crude material purified by column chromatography

Sources & evidence

ORD record
ord-2d367ac8de2744dba3e0fcb46f27a7b8
Source dataset
uspto-grants-2014_11
Patent number
US08883827B2

Reaction notes

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