1,1'-Carbonyldiimidazole → 2-[2-Oxo-1-phenyl-2-[(2,4,6-trimethoxyphenyl)amino]ethyl]tridecanoic acid hydrazide

HRID 1756981Notes

Reaction equation

HRID 1756981 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([O:11][CH3:12])[C:4]=1[NH:13][C:14]([CH:16]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)C(O)=O)=[O:15].C(N1C=CN=C1)(N1C=CN=C1)=O.[C:38]([NH:52][NH2:53])(=[O:51])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50]>C1COCC1>[O:15]=[C:14]([NH:13][C:4]1[C:5]([O:11][CH3:12])=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:3]=1[O:2][CH3:1])[CH:16]([CH:39]([CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[C:38]([NH:52][NH2:53])=[O:51])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 10665192alpha-[[(2,4,6-Trimethoxyphenyl)amino]carbonyl]benzene acetic acidHCID 10823265Tridecanoic acid hydrazide

Product 1

HCID 695611992-[2-Oxo-1-phenyl-2-[(2,4,6-trimethoxyphenyl)amino]ethyl]tridecanoic acid hydrazide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of α-[[(2,4,6-trimethoxyphenyl)amino]-carbonyl]-benzene acetic acid (46.73 g, 0.1353 mol), and 1,1'-carbonyldiimidazole (24.7 g, 0.152 mol) in dry THF (1.0 L) was stirred at room temperature under nitrogen for 2 hours. A white solid precipitated. To the suspension was added tridecanoic acid hydrazide (30.90 g, 0.1353 mol), and the mixture was stirred at room temperature for 17 hours, then at 40° C. for 21 hours. The mixture was chilled (+5° C.) and filtered. The filtercake was washed (THF, ether, water) and dried under house vacuum/air stream; yield 54.36 g (72%); mp 175°-180° C.

Workup

  1. customA white solid precipitated
  2. waitat 40° C. for 21 hours
  3. temperatureThe mixture was chilled (+5° C.)
  4. filtrationfiltered
  5. washThe filtercake was washed (THF, ether, water)
  6. customdried under house vacuum/air stream

Sources & evidence

ORD record
ord-b8a5938c413c4dca9083006b79575ddb
Source dataset
uspto-grants-1995_08
Patent number
US05441975

Reaction notes

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