Methyl 4-(chlorocarbonyl)benzoate → HCID 22713233, compound

HRID 351551Notes

Reaction equation

HRID 351551 reaction equation
[CH2:1]([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([NH:18][NH2:19])=[O:17])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH3:20][O:21][C:22]([C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1)=[O:23]>O1CCCC1.N1C=CC=CC=1>[CH2:1]([O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][C:16]([NH:18][NH:19][C:28](=[O:29])[C:27]2[CH:26]=[CH:25][C:24]([C:22]([O:21][CH3:20])=[O:23])=[CH:32][CH:31]=2)=[O:17])=[CH:12][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 22713193HCID 22713193, compound

Product 1

HCID 22713233HCID 22713233, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 3-(4-n-hexyloxyphenyl)propiono-hydrazide (0.92 g) in tetrahydrofuran (25 ml) and pyridine (0.84 ml) was added a solution of 4-methoxycarbonylbenzoyl chloride (0.73 g) in tetrahydrofuran (10 ml) dropwise at 5° C. The reaction mixture was stirred for 1 hour and poured into ice-water. The precipitate was collected by filtration, washed with water and dried under reduced pressure to give 1-[3-(4-n-hexyloxyphenyl)propanoyl]-2-(4-methoxycarbonylbenzoyl)hydrazine (1.43 g).

Workup

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

Sources & evidence

ORD record
ord-49c7deb4e0514b99ab22ab81317e472b
Source dataset
uspto-grants-2004_06
Patent number
US06743776B2

Reaction notes

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