Water → HCID 19743503, compound

HRID 2254033Notes

Reaction equation

HRID 2254033 reaction equation
[K].[Cl:2][C:3]1[CH:19]=[CH:18][C:6]2[N:7]=[C:8]([O:10][C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[O:9][C:5]=2[CH:4]=1.[C:20]([CH:22]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=1[Cl:35])[C:23](=[O:27])[CH:24](Cl)[CH3:25])#[N:21].O>CN(C)C=O>[C:20]([CH:22]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=1[Cl:35])[C:23](=[O:27])[CH:24]([O:17][C:14]1[CH:13]=[CH:12][C:11]([O:10][C:8]2[O:9][C:5]3[CH:4]=[C:3]([Cl:2])[CH:19]=[CH:18][C:6]=3[N:7]=2)=[CH:16][CH:15]=1)[CH3:25])#[N:21]

Participants

6

Reactant 4

HCID 962WaterHCID 155475Phenol, 4-((6-chloro-2-benzoxazolyl)oxy)-HCID 5462222PotassiumHCID 197435991-Cyano-1-(2,4-dichlorophenyl)-3-chloro-2-butanone

Product 1

HCID 19743503HCID 19743503, compoundYield 46.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2.70 Grams of a potassium salt of 4-(6-chloro-2-benzoxazolyloxy)phenol and 2.48 g of 1-cyano-1-(2,4-dichlorophenyl)-3-chloro-2-butanone were refluxed in 50 ml of N,N-dimethylformamide under heat at 100° C. for 4 hours. The reaction mixture was added to water, and after the mixture was subjected to extraction with chloroform, the extract was concentrated. The residue was separated and purified by column chromatography to give 2.05 g of a compound No. 176 which was a light yellow solid (melting point 93°-94° C.). The yield was 46.9%. The compound No. 176 was analyzed, and the results are shown in Tables 1 to 23.

Workup

  1. extractionafter the mixture was subjected to extraction with chloroform
  2. concentrationthe extract was concentrated
  3. customThe residue was separated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-3c209366620e4fa698b926cccc96231f
Source dataset
uspto-grants-1993_08
Patent number
US05234894

Reaction notes

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