Chloroacetyl chloride → HCID 57951265, compound

HRID 1360840Notes

Reaction equation

HRID 1360840 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[C:8]2[N:9]=[C:10]([NH2:12])[S:11][C:7]=2[C:6]2[CH:13]=[N:14][NH:15][C:5]=2[CH:4]=1.[Cl:18][CH2:19][C:20](Cl)=[O:21]>O1CCOCC1>[Cl:18][CH2:19][C:20]([NH:12][C:10]1[S:11][C:7]2[C:6]3[CH:13]=[N:14][N:15]([C:20](=[O:21])[CH2:19][Cl:18])[C:5]=3[CH:4]=[C:3]([C:2]([F:1])([F:16])[F:17])[C:8]=2[N:9]=1)=[O:21]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 57951259HCID 57951259, compound

Product 1

HCID 57951265HCID 57951265, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 0.26 g (1.00 mmol) of 4-trifluoromethyl-6H-pyrazolo[4′,3′:3,4]benzo[1,2-d]thiazol-2-ylamine, 1.0 ml (12.6 mmol) of chloroacetyl chloride and 4 ml of 1,4-dioxane was heated under reflux for 3 hours. After the completion of the reaction was confirmed by HPLC, the reaction mixture was cooled to room temperature and poured into ice-water. The precipitated solid was collected by filtration and was washed with water to give 0.34 g (yield: 77%) of 2-chloro-N-[6-(2-chloro-acetyl)-4-trifluoromethyl-6H-pyrazolo[4′,3′:3,4]benzo[1,2-d]thiazol-2-yl]-acetamide.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. filtrationThe precipitated solid was collected by filtration
  4. washwas washed with water

Sources & evidence

ORD record
ord-128fa6fd101c4040952d276292a173c0
Source dataset
uspto-grants-2011_02
Patent number
US07879887B2

Reaction notes

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