Chloroacetyl chloride → 5-Bromo-N'-(chloroacetyl)-3-pyridinecarbohydrazide

HRID 913401Notes

Reaction equation

HRID 913401 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:10][NH2:11])=[O:9])[CH:5]=[N:6][CH:7]=1.CN1CCOCC1.[Cl:19][CH2:20][C:21](Cl)=[O:22]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:10][NH:11][C:21](=[O:22])[CH2:20][Cl:19])=[O:9])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 79724-MethylmorpholineHCID 6963655-Bromonicotinohydrazide

Product 1

HCID 578003225-Bromo-N'-(chloroacetyl)-3-pyridinecarbohydrazideYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold suspension of 5-bromo-3-pyridinecarbohydrazide (3.0 g, 13.88 mmol) in anhydrous CH2Cl2 (60 mL) was added 4-methyl-morpholine (2.1 g, 20.82 mmol), followed by dropwise addition of chloroacetyl chloride (1.88 g, 16.67 mmol). The cold bath was then removed and the mixture stirred at rt for 15 h. Heavy precipitation occurred and the mixture was diluted with additional CH2Cl2 (50 mL) and stirring continued for 24 h. The solids were collected by filtration and washed with CH2Cl2 to afford the title compound (3.66 g, 90% yield): MS (ES) m/z 292 and 294 (M+1 Br isotopes).

Workup

  1. customThe cold bath was then removed
  2. customHeavy precipitation
  3. additionthe mixture was diluted with additional CH2Cl2 (50 mL)
  4. stirringstirring
  5. waitcontinued for 24 h
  6. filtrationThe solids were collected by filtration
  7. washwashed with CH2Cl2

Sources & evidence

ORD record
ord-a25ef43941ae48b9a9b20cf74c6d7d49
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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