Water → HCID 53736551, compound

HRID 1684638Notes

Reaction equation

HRID 1684638 reaction equation
[C:1]1([C:7]2[O:8][CH:9]=[C:10]([CH2:12][CH2:13][O:14][C:15]3[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:24][NH:25][C:26]([NH2:28])=[O:27].CC([O-])=O.[Na+].O>CO>[C:1]1([C:7]2[O:8][CH:9]=[C:10]([CH2:12][CH2:13][O:14][C:15]3[CH:22]=[CH:21][C:18]([CH:19]=[N:24][NH:25][C:26]([NH2:28])=[O:27])=[CH:17][CH:16]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11236Semicarbazide hydrochlorideHCID 517045Sodium AcetateHCID 10685112HCID 10685112, compound

Product 1

HCID 53736551HCID 53736551, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 20.0 g of aldehyde from Example 17 Part A, 8.29 g of semicarbazide hydrochloride, 8.14 g of NaOAc and 150 mL of H2O was heated for 0.75 hours at 100° C. with occasional swirling. The heterogenous mixture was diluted with 150 mL of MeOH and allowed to stand at 25° C. for 64 hours. The solid was filtered and washed with H2O, refluxed with 500 mL of MeOH and filtered hot leaving 21.3 g of 4-(2-(2-phenyl-4-oxazolyl)ethoxy)benzaldehyde semicarbazone (89%, m.p. 221°-226° C.).

Workup

  1. filtrationThe solid was filtered
  2. washwashed with H2O
  3. temperaturerefluxed with 500 mL of MeOH
  4. filtrationfiltered hot

Sources & evidence

ORD record
ord-692e1a11de8f4ff2801079257c64e1a5
Source dataset
uspto-grants-1997_06
Patent number
US05641796

Reaction notes

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