tert-Butyl carbazate → 1,1-Dimethylethyl 2-[(2-chloro-4-fluorophenyl)acetyl]hydrazinecarboxylate

HRID 1097714Notes

Reaction equation

HRID 1097714 reaction equation
[Cl: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>[Cl: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 2757568(2-Chloro-4-fluorophenyl)acetyl chloride

Product 1

HCID 668130061,1-Dimethylethyl 2-[(2-chloro-4-fluorophenyl)acetyl]hydrazinecarboxylateYield 64.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-chloro-4-fluorophenylacetyl chloride (10 mmol) in dry DCM (15 ml) was added over 20 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 a further 2 h, the mixture was washed with 1M HCl then with aqueous NaHCO3. A white solid precipitated at this point, which was filtered off, washed with water and DCM then dried to yield 1,1-dimethylethyl 2-[(2-chloro-4-fluorophenyl)acetyl]hydrazinecarboxylate (1.94 g).

Workup

  1. washthe mixture was washed with 1M HCl
  2. customA white solid precipitated at this point, which
  3. filtrationwas filtered off
  4. washwashed with water and DCM
  5. customthen dried

Sources & evidence

ORD record
ord-f73a78a286de418b8d486f62fa06453a
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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