Dimethylformamide → 4Iodo-benzoic acid N'-(2,2-dimethyl-propionyl)-hydrazide

HRID 31409

Reaction equation

HRID 31409 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.C(O[C:16]([CH3:19])([CH3:18])[CH3:17])(=O)NN.C[N:21](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.C[N:64](C)[CH:65]=[O:66]>>[CH3:17][C:16]([CH3:19])([CH3:18])[C:65]([NH:64][NH:21][C:6](=[O:8])[C:5]1[CH:4]=[CH:3][C:2]([I:1])=[CH:10][CH:9]=1)=[O:66]

Participants

7

Reactant 6

HCID 6228DimethylformamideHCID 120854-Iodobenzoic acidHCID 70091tert-Butyl carbazateHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 693159064Iodo-benzoic acid N'-(2,2-dimethyl-propionyl)-hydrazide

Procedure

4-Iodobenzoic acid (5 g, 20.2 mmol) was dissolved in dimethylformamide (50 ml). To this was added tert-butyl carbazate (2.66 g, 20.2 mmol), HATU (9.2 g, 24.2 mmol), 1-hydroxybenzotriazole (2.7 g, 20.2 mmol) and N,N-diisopropylethylamine (10.5 ml, 60.5 mmol). The mixture was stirred for 17 hours at room temperature. The solvent was removed in vacuo and the residue partitioned between dichloromethane (75 ml) and saturated aqueous sodium bicarbonate solution (75 ml). The organic layer was washed with water (100 ml), brine (100 ml), dried over magnesium sulfate, filtered and the solvent removed in vacuo. The desired product was obtained as a cream solid (4.6 g, 12.7 mmol).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between dichloromethane (75 ml) and saturated aqueous sodium bicarbonate solution (75 ml)
  3. washThe organic layer was washed with water (100 ml), brine (100 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-42cdd1f4f85041759000fb71106a03b8
Source dataset
uspto-grants-2008_09
Patent number
US07425555B2

Linked notes

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