Triethylamine → HCID 22853537, compound

HRID 36718Notes

Reaction equation

HRID 36718 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:11](Cl)=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.[CH:14]([C@@H:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]1[NH2:24])([CH2:16][CH3:17])[CH3:15].C(N(CC)CC)C>O1CCCC1.O>[CH:14]([C@@H:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]1[NH:24][C:11]([C:4]1[S:3][C:2]([CH3:1])=[N:6][C:5]=1[C:7]([F:10])([F:9])[F:8])=[O:12])([CH2:16][CH3:17])[CH3:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 146010812-Methyl-4-(trifluoromethyl)-5-thiazolecarbonyl chlorideHCID 22853538HCID 22853538, compound

Product 1

HCID 22853537HCID 22853537, compoundYield 44.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

At 0° C., 3.4 g of 2-methyl-4-trifluoromethylthiazole-5-carboxylic chloride is dripped into a solution of 2.3 g of trans-2-sec.-butylcyclohexylamine and 1.5 g of triethylamine in 15 ml of tetrahydrofuran, and the mixture is stirred for 2 hours at 25° C. The batch is diluted with 300 ml of water, extracted twice with tert-butyl methyl ether and dried, the solvent is evaporated off, and the residue is made into a paste with a small amount of pentane. There is isolated 2.3 g of 2-methyl-4-trifluoromethyl-thiazole-5-carboxylic acid-trans-2-sec-butylcyclohexylamide of m.p. 112°-113° C.

Workup

  1. customAt 0° C.
  2. extractionextracted twice with tert-butyl methyl ether
  3. customdried
  4. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-d4f28348effc4e01a5f9475c99cf50a6
Source dataset
uspto-grants-1995_05
Patent number
US05416103

Reaction notes

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