Water → N'-(4-iodobenzoyl)-3-methoxybenzohydrazide

HRID 2278459Notes

Reaction equation

HRID 2278459 reaction equation
[I:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17](Cl)=[O:18].N1C=CC=CC=1.O>C1COCC1>[I:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH:9][C:17](=[O:18])[C:16]2[CH:20]=[CH:21][CH:22]=[C:14]([O:13][CH3:12])[CH:15]=2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 74374m-Anisoyl chloride3×HCID 3061044-Iodobenzenecarbohydrazide

Product 1

HCID 67510202N'-(4-iodobenzoyl)-3-methoxybenzohydrazide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-Iodobenzohydrazide (5.0 g, 19.1 mmol) in dry THF (80.0 ml) was slowly added 3-methoxybenzoyl chloride (3.5 g, 20.5 mmol) at 0° C. under nitrogen. During addition of 3-methoxybenzoyl chloride the white solid was appeared. After addition of 3-methoxybenzoyl chloride, the reaction was warmed up to room temperature. The reaction mixture was stirred for 18 hours at room temperature and then pyridine (5.0 ml) was added and stirred for additional 2 h. Water (300.0 ml) was added to reaction mixture. The white solid was obtained and collected by filtration. After dried under vacuum, product was obtained as white powder in 7.2 g (94.7%). 1H NMR (400 MHz, DMSO-d6, δ): 10.60 (s, 1H, NH), 10.52 (s, 1H, NH), 7.91 (d, J=8.0 Hz, 2H), 7.68 (d, J=8.0 Hz, 2H), 7.50 (d, J=8.0 Hz, 1H), 7.45 (d, J=2.4 Hz, 1H), 7.41 (d, J=8.0 Hz, 1H), 7.15 (dd, J1=8.0 Hz, J2=2.4 Hz, 1H), 3.81 (s, 3H, OCH3).

Workup

  1. customat 0° C.
  2. stirringstirred for additional 2 h
  3. customThe white solid was obtained
  4. filtrationcollected by filtration
  5. customAfter dried under vacuum
  6. customproduct was obtained as white powder in 7.2 g (94.7%)

Sources & evidence

ORD record
ord-b795313339694a68a88f355ca0ab7904
Source dataset
uspto-grants-2015_09
Patent number
US09133177B2

Reaction notes

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