2-Amino-4-(trifluoromethyl)benzenethiol → Ethyl 5-(trifluoromethyl)-2-benzothiazolecarboxylate

HRID 29448

Reaction equation

HRID 29448 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[SH:12].[CH2:13]([O:15][C:16](OCC)([O:22]CC)[C:17](OCC)=O)[CH3:14]>>[CH2:13]([O:15][C:16]([C:17]1[S:12][C:3]2[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=2[N:1]=1)=[O:22])[CH3:14]

Participants

3

Reactant 2

HCID 880422-Amino-4-(trifluoromethyl)benzenethiolHCID 5090273Ethyl 2,2,2-triethoxyacetate

Product 1

HCID 55189808Ethyl 5-(trifluoromethyl)-2-benzothiazolecarboxylate

Conditions

Temperature
110 °C

Procedure

To 2-amino-4-trifluoromethyl-benzenethiol (0.7 g) was added ethyl triethoxyacetate (3 eq). The mixture was stirred at 110° C. overnight. The reaction mixture was cooled and triturated with hexane. Filtration gave 460 mg of 5-trifluoromethyl-benzothiazole-2-carboxylic acid ethyl ester as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customtriturated with hexane
  3. filtrationFiltration

Sources & evidence

ORD record
ord-0b562ebc862241489a596e1f9fcc353b
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Linked notes

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