Water → 1-(4-n-Hexyloxybenzoyl)-2-(4-methoxycarbonylbenzoyl)hydrazine

HRID 1386615Notes

Reaction equation

HRID 1386615 reaction equation
[CH2:1]([O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([NH:14][NH2:15])=[O:13])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].N1C=CC=CC=1.[Cl-].[CH3:25][O:26][C:27](=[O:37])[C:28]1[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=1.O>O1CCCC1>[CH2:1]([O:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([NH:14][NH:15][C:32](=[O:33])[C:31]2[CH:30]=[CH:29][C:28]([C:27]([O:26][CH3:25])=[O:37])=[CH:36][CH:35]=2)=[O:13])=[CH:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 16259404-(Hexyloxy)benzohydrazideHCID 53442854Terephthalic acid monomethylester chloride

Product 1

HCID 171784121-(4-n-Hexyloxybenzoyl)-2-(4-methoxycarbonylbenzoyl)hydrazineYield 103.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-n-Hexyloxybenzoylhydrazine (1.96 g) and pyridine (0.74 ml) in tetrahydrofuran (20 ml) was added a solution of terephthalic acid monomethyl ester chloride (1.56 g) in tetrahydrofuran (15 ml) dropwise at 0° C. The reaction mixture was stirred at room temperature for 2 hours, and poured into water. The precipitate was collected by filtration and washed with acetonitrile. The residue was dried under reduced pressure to give 1-(4-n-Hexyloxybenzoyl)-2-(4-methoxycarbonylbenzoyl)hydrazine (2.99 g).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with acetonitrile
  3. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-85d5ed45cce246f7bc6cc73fcef7b9c4
Source dataset
uspto-grants-2001_07
Patent number
US06265536B1

Reaction notes

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