Water → HCID 19375992, compound

HRID 1656410Notes

Reaction equation

HRID 1656410 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:13]=[C:14]([C:17]([NH2:19])=O)[S:15][CH:16]=2)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9].FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:13]=[C:14]([C:17]#[N:19])[S:15][CH:16]=2)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 9845Trifluoroacetic anhydrideHCID 19375961HCID 19375961, compound

Product 1

HCID 19375992HCID 19375992, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-(3-chloro-4,5-dimethoxyphenyl)-thiazole-2-carboxamide (1.58 g) (Example 1c) in pyridine (9 ml) was cooled to 0° C. and treated with trifluoroacetic anhydride (4 ml) whilst maintaining the internal temperature below 10° C. The mixture was stirred at room temperature for 10 min, then cooled and treated dropwise with water (45 ml) whilst maintaining the internal temperature below 30° C. The precipitated solid was collected by filtration and dried under vacuum at 60° C. Recrystallisation from dichloromethane-ether afforded 4-(3-chloro-4,5-dimethoxyphenyl)-thiazole-2-carbonitrile (1.25 g), m.p. 147°-149° C.

Workup

  1. temperaturewhilst maintaining the internal temperature below 10° C
  2. temperaturecooled
  3. temperaturewhilst maintaining the internal temperature below 30° C
  4. filtrationThe precipitated solid was collected by filtration
  5. customdried under vacuum at 60° C
  6. customRecrystallisation from dichloromethane-ether

Sources & evidence

ORD record
ord-59ed6ab1abed485fb4faef4b66b9cd94
Source dataset
uspto-grants-1993_10
Patent number
US05254575

Reaction notes

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