Water → 3,5-diiodo-N'-(3-methoxybenzoyl)benzohydrazide

HRID 2278470Notes

Reaction equation

HRID 2278470 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([I:12])[CH:11]=1)[C:5]([NH:7][NH2:8])=[O:6].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18](Cl)=[O:19].N1C=CC=CC=1.O>C1COCC1.CN(C=O)C>[I:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([I:12])[CH:11]=1)[C:5]([NH:7][NH:8][C:18](=[O:19])[C:17]1[CH:21]=[CH:22][CH:23]=[C:15]([O:14][CH3:13])[CH:16]=1)=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 74374m-Anisoyl chloride2×HCID 67511905N-hydroxy-3,5-diiodobenzamide

Product 1

HCID 675103133,5-diiodo-N'-(3-methoxybenzoyl)benzohydrazide

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a solution of 3,5-Diiodobenzohydrazide (4.5 g, 11.60 mmol) in dry THF/DMF (100.0 ml:24.0 ml) was slowly added 3-methoxybenzoyl chloride (2.2 g, 12.90 mmol) at 0° C. under nitrogen. After addition of 3-methoxybenzoyl chloride, the reaction was warmed up to room temperature. The reaction mixture was stirred for 19 hours at room temperature and then pyridine (5.0 ml) was added and stirred for additional 1 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 5.05 g (83.3%). 1H NMR (400 MHz, DMSO-d6, δ): 10.72 (s, 1H, NH), 10.62 (s, br, 1H, NH), 8.33 (t, J=1.6 Hz, 1H), 8.23 (d, J=1.6 Hz, 2H), 7.50-7.41 (m, 3H), 7.15 (m, 1H), 3.81 (s, 3H, OCH3).

Workup

  1. customat 0° C.
  2. stirringstirred for additional 1 h
  3. customThe white solid was obtained
  4. filtrationcollected by filtration
  5. customAfter dried under vacuum
  6. customproduct was obtained as white powder in 5.05 g (83.3%)

Sources & evidence

ORD record
ord-b72c713bb11f4898a07b321f1c42bd27
Source dataset
uspto-grants-2015_09
Patent number
US09133177B2

Reaction notes

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