Chloroacetamide → HCID 21712127, compound

HRID 650500Notes

Reaction equation

HRID 650500 reaction equation
[Cl:1][C:2]1[C:3]([OH:20])=[N:4][C:5]([C:9]2[C:13]([Cl:14])=[C:12]([O:15][CH:16]([F:18])[F:17])[N:11]([CH3:19])[N:10]=2)=[C:6]([F:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:28][C:29]([NH2:31])=[O:30]>>[Cl:1][C:2]1[C:3]([O:20][CH2:28][C:29]([NH2:31])=[O:30])=[N:4][C:5]([C:9]2[C:13]([Cl:14])=[C:12]([O:15][CH:16]([F:17])[F:18])[N:11]([CH3:19])[N:10]=2)=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 3

HCID 6580ChloroacetamideHCID 11430Potassium CarbonateHCID 178481775HCID 178481775, compound

Product 1

HCID 21712127HCID 21712127, compoundYield 86%

Conditions

Temperature
50 °C

Procedure

20.0 g of 3-chloro-6-(4-chloro-5-difluoromethoxy-1-methyl-[1H]-pyrazol-3-yl)-5-fluoropyridin-2-ol (Example P27) are placed together with 18.9 g of potassium carbonate and 6.4 g of chloroacetamide at 22° C. and the mixture is stirred overnight at 50° C. The next day, the mixture is cooled to 22° C. and then introduced into 2 liters of ice-water. After subsequently stirring for 10 minutes at 22° C., the resulting slurry is filtered. The filtration residue is washed with cold water and then dried in vacuo at 60° C. 20.2 g of the desired title compound are obtained in the form of a white solid having a melting point of 178-180° C.

Workup

  1. temperatureThe next day, the mixture is cooled to 22° C.
  2. stirringAfter subsequently stirring for 10 minutes at 22° C.
  3. filtrationthe resulting slurry is filtered
  4. washThe filtration residue is washed with cold water
  5. customdried in vacuo at 60° C

Sources & evidence

ORD record
ord-738598b3a060457282d62b00ab119d07
Source dataset
uspto-grants-2001_08
Patent number
US06274536B1

Reaction notes

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