Water → 2-[6-carboxybenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide

HRID 1091670Notes

Reaction equation

HRID 1091670 reaction equation
[C:1]([C:4]1[CH:25]=[CH:24][C:7]2[NH:8][C:9](=[C:11]([C:14]3[N:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][N:15]=3)[C:12]#[N:13])[S:10][C:6]=2[CH:5]=1)([OH:3])=[O:2].[OH2:26]>S(=O)(=O)(O)O>[C:1]([C:4]1[CH:25]=[CH:24][C:7]2[NH:8][C:9](=[C:11]([C:14]3[N:19]=[C:18]([C:20]([F:23])([F:21])[F:22])[CH:17]=[CH:16][N:15]=3)[C:12]([NH2:13])=[O:26])[S:10][C:6]=2[CH:5]=1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 962WaterHCID 665935462-[6-carboxybenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethyl-pyrimidin-2-yl)acetonitrile

Product 1

HCID 665935492-[6-carboxybenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamideYield 90%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2-[6-carboxybenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)-acetonitrile (620 mg, 1.70 mmol) in concentrated sulfuric acid (5 mL), was heated to 50° C. for 10 hr. The mixture was cooled to room temperature and added dropwise to rapidly stirred room-temperature water (100 mL). The precipitate that formed was collected by filtration, washed with water and hexanes, and dried under vacuum to give 2-[6-carboxybenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide (587 mg, 90% yield) as a brown solid.

Workup

  1. customThe precipitate that formed
  2. filtrationwas collected by filtration
  3. washwashed with water and hexanes
  4. customdried under vacuum

Sources & evidence

ORD record
ord-4186b1c49c874e67bdb7252bc012673d
Source dataset
uspto-grants-2012_03
Patent number
US08129396B2

Reaction notes

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