Isopropylamine → Ethyl 2-(isopropylamino)-4-(trifluoromethyl)thiazole-5-carboxylate

HRID 359290Notes

Reaction equation

HRID 359290 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].Cl[C:6]1[S:7][C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:9]([C:11]([F:14])([F:13])[F:12])[N:10]=1>C(#N)C>[CH3:2][CH:1]([NH:4][C:6]1[S:7][C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:9]([C:11]([F:13])([F:12])[F:14])[N:10]=1)[CH3:3]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 1235240Ethyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate

Product 1

HCID 7174201Ethyl 2-(isopropylamino)-4-(trifluoromethyl)thiazole-5-carboxylateYield 42.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

By the procedure of Example 39, a stirred mixture of 10 ml acetonitrile, 2.28 g (38.6 mmol) of iso-propylamine, and 5 g (19.3 mmol) of ethyl 2-chloro-4-trifluoromethyl-5-thiazolecarboxylate (prepared as described in U.S. Pat. No. 4,199,506), was heated at reflux for 16 hours. The product was separated and then recrystallized in hexane to yield 2.30 g of a beige solid product (m.p.=94°-97° C.) identified in Table 1.

Workup

  1. customprepared
  2. temperature4,199,506), was heated
  3. temperatureat reflux for 16 hours
  4. customThe product was separated
  5. customrecrystallized in hexane

Sources & evidence

ORD record
ord-0029207d60cf4c5d934520548cd0e229
Source dataset
uspto-grants-1991_03
Patent number
US05000775

Reaction notes

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