Water → N'-(3-Iodobenzoyl)-3-methoxybenzohydrazide

HRID 2278465Notes

Reaction equation

HRID 2278465 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([NH:7][NH2:8])=[O:6].[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.CN(C=O)C>[I:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([NH:7][NH:8][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][CH:22]=[C:14]([O:13][CH3:12])[CH:15]=1)=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 74374m-Anisoyl chloride3×HCID 6157743-Iodobenzohydrazide

Product 1

HCID 585044N'-(3-Iodobenzoyl)-3-methoxybenzohydrazide

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a solution of 3-iodobenzohydrazide (10.0 g, 38.16 mmol) in dry THF/DMF (100.0 ml:10.0 ml) was slowly added 3-methoxybenzoyl chloride (7.0 g, 42.03 mmol) at 0° C. under nitrogen. During addition of 3-methoxybenzoyl chloride, white solid was appeared. After addition of 3-methoxybenzoyl chloride, the reaction was allowed to warm up to room temperature. The reaction mixture was stirred for 19 hours at room temperature and then pyridine (20.0 ml) was added and stirred for additional 45 min. Water (300.0 ml) was added to reaction mixture. The white solid was obtained and collected by filtration and washed with water. After dried under vacuum, product was obtained as white powder in 12.4 g (82.0%). 1H NMR (400 MHz, DMSO-d6, δ): 10.62 (s, 1H, NH), 10.56 (s, 1H, NH), 8.25 (t, J=1.6 Hz, 1H), 7.96 (d, J=8.0 Hz, 1H), 7.91 (d, J=8.0 Hz, 1H), 7.49 (d, J=8.0 Hz, 1H), 7.45 (d, J=2.4 Hz, 1H), 7.41 (d, J=8.0 Hz, 1H), 7.34 (t, J=8.0 Hz, 1H), (dd, J1=8.0 Hz, J2=2.4 Hz, 1H), 3.81 (s, 3H, OCH3).

Workup

  1. customat 0° C.
  2. stirringstirred for additional 45 min
  3. customThe white solid was obtained
  4. filtrationcollected by filtration
  5. washwashed with water
  6. customAfter dried under vacuum
  7. customproduct was obtained as white powder in 12.4 g (82.0%)

Sources & evidence

ORD record
ord-f48fb629c0fa403185cc96293bfcd2ad
Source dataset
uspto-grants-2015_09
Patent number
US09133177B2

Reaction notes

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