tert-Butyl carbazate → Tert-butyl 2-(2-(2,4-difluorophenyl)acetyl)hydrazinecarboxylate

HRID 1097716Notes

Reaction equation

HRID 1097716 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10](Cl)=[O:11].[C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:16])[NH:14][NH2:15].CCN(C(C)C)C(C)C>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([NH:15][NH:14][C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:11]

Participants

5

Reactant 3

HCID 70091tert-Butyl carbazateHCID 81531DiisopropylethylamineHCID 152316062,4-Difluorophenylacetyl chloride

Product 1

HCID 66812950Tert-butyl 2-(2-(2,4-difluorophenyl)acetyl)hydrazinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2,4-difluorophenylacetyl chloride (10 mmol) in dry DCM (15 ml) was added over 10 min. to a mixture of t-butyl carbazate (1.32 g, 10 mmol) and DIPEA (1.77 ml, 10.2 mmol) in dry DCM (20 ml). After stirring for 1.5 h the mixture was washed with 1M HCl then with aqueous NaHCO3. The organic phase was evaporated to afford 1,1-dimethylethyl 2-[(2,4-difluorophenyl)acetyl]hydrazinecarboxylate as a white solid.

Workup

  1. washwas washed with 1M HCl
  2. customThe organic phase was evaporated

Sources & evidence

ORD record
ord-c54f5a3bceeb41039d787e915ecaf3ce
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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