tert-Butyl carbazate → N'-(2-fluoro-4-nitrobenzoyl)hydrazinecarboxylic acid tert-butyl ester

HRID 723880Notes

Reaction equation

HRID 723880 reaction equation
C(N(CC)C(C)C)(C)C.[F:10][C:11]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=O.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[C:47]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])(=[O:50])[NH:48][NH2:49]>CN(C=O)C>[C:52]([O:51][C:47]([NH:48][NH:49][C:13](=[O:15])[C:12]1[CH:16]=[CH:17][C:18]([N+:20]([O-:22])=[O:21])=[CH:19][C:11]=1[F:10])=[O:50])([CH3:55])([CH3:54])[CH3:53]

Participants

6

Reactant 4

HCID 70091tert-Butyl carbazateHCID 81531DiisopropylethylamineHCID 3026792-Fluoro-4-nitrobenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 68487050N'-(2-fluoro-4-nitrobenzoyl)hydrazinecarboxylic acid tert-butyl esterYield 57.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N, N-Diisopropylethylamine (14.1 ml, 0.081 mol) is added to 2-fluoro-4-nitrobenzoic acid (5 g, 0.027 mol) and O-(7-azabenzotriazol-1-yl)-N, N, N′, N′-tetramethyluronium hexafluorophosphate (10.8 g, 0.0284 mol) in DMF (100 ml) and the mixture stirred at room temperature for 20 minutes. tert-Butyl carbazate (3.57 g, 0.0270 mol) is added in one portion and the reaction stirred overnight at room temperature. The mixture is concentrated and diluted with water (100 ml). The resulting precipitate is filtered, washed well with water, and dried under vacuum to give the title compound as a white solid (4.63 g, 57%), [M+H]+=300.

Workup

  1. stirringthe reaction stirred overnight at room temperature
  2. concentrationThe mixture is concentrated
  3. additiondiluted with water (100 ml)
  4. filtrationThe resulting precipitate is filtered
  5. washwashed well with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-d0a52783ab1843048cdf7176cd834d9f
Source dataset
uspto-grants-2006_11
Patent number
US07141588B2

Reaction notes

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