Triethylamine → 4-Chloro-benzoic acid N'-(4-amino-3-nitro-benzoyl)-hydrazide

HRID 1360736Notes

Reaction equation

HRID 1360736 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][C:14]=1[N+:22]([O-:24])=[O:23].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C(N(CC)CC)C>CN(C=O)C.O>[NH2:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([NH:9][NH:8][C:6](=[O:7])[C:5]2[CH:10]=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:18])=[CH:15][C:14]=1[N+:22]([O-:24])=[O:23]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 108164-ChlorobenzohydrazideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 74115Benzoic acid, 4-amino-3-nitro-HCID 757711-Hydroxybenzotriazole

Product 1

HCID 466515574-Chloro-benzoic acid N'-(4-amino-3-nitro-benzoyl)-hydrazide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 4-Chloro-benzoic acid hydrazide (5.0 g, 29 mmol) and 4-Amino-3-nitro-benzoic acid (5.3 g, 29 mmol) in DMF (100 mL) was added HOBT (3.9 g, 29 mmol), and EDCI (5.5 g, 29 mmol), followed by triethylamine (12.1 mL, 87 mmol). The mixture was stirred at ambient temperature for 18 hours. Water (50 mL) was added to the reaction mixture. The precipitate was collected by filtration, washed with water, and dried under vacuum to provide the title compound as a yellow solid. 1H NMR (DMSO-d6, 400 MHz) δ ppm 7.08 (d, J=8.97 Hz, 1H) 7.61 (m, 2H) 7.82-7.97 (m, 5H) 8.66 (d, J=2.15 Hz, 1H) 10.52 (s, 1H) 10.57 (s, 1H; (M+H)+=335.0

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-2a01f674869445a98f4c6a5f6d5dab8d
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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