Water → HCID 21058038, compound

HRID 2216401Notes

Reaction equation

HRID 2216401 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].CC(C)([O-])C.[K+].Cl[CH2:19][C:20]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=1[Cl:30])=[O:21].O>CN(C)C=O.[O-]CC.[Na+]>[NH2:5][C:4]1[C:3]2[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[CH:9][C:2]=2[O:1][C:19]=1[C:20]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=1[Cl:30])=[O:21]

Participants

7

Reactant 4

HCID 962WaterHCID 2259982-Chloro-N-(2,4-dichlorophenyl)acetamideHCID 114236802-Hydroxy-4-methoxybenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 21058038HCID 21058038, compound

Reagents, catalysts & solvents 2

HCID 2723922Sodium ethoxideCatalystHCID 6228DimethylformamideSolvent

Procedure

2-Hydroxy-4-methoxybenzonitrile (3 g) synthesized according to the method described in JP-A-8-253466 was dissolved in dimethylformamide (20 ml) and potassium tert-butoxide (5 g) was added under ice-cooling. After stirring for 30 min, 2-chloro-N-(2,4-dichlorophenyl)acetamide was added and the mixture was further stirred for 1 hr. Then water (20 ml) was added and the crystals were precipitated. The crystals were added to ethanol (20 ml) to give a solution, to which sodium ethoxide (0.6 mg) was added. The mixture was stirred at 78° C. for 1 hr and cooled to give the title compound (1.36 g). melting point: 187-188° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 1 hr
  3. customthe crystals were precipitated
  4. additionThe crystals were added to ethanol (20 ml)
  5. customto give a solution
  6. stirringThe mixture was stirred at 78° C. for 1 hr
  7. temperaturecooled

Sources & evidence

ORD record
ord-4ffc20199d8345e5bc637ec096c85091
Source dataset
uspto-grants-2006_09
Patent number
US07112594B2

Reaction notes

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