Triethylamine → 2-Ethoxycarbonylamino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazole

HRID 974041Notes

Reaction equation

HRID 974041 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([F:21])[CH:10]=2)[CH3:8])[N:6]=1.Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24].C(N(CC)CC)C>O1CCCC1.O>[CH2:26]([O:25][C:23]([NH:1][C:2]1[S:3][CH:4]=[C:5]([CH:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[C:11]([F:21])[CH:10]=2)[CH3:8])[N:6]=1)=[O:24])[CH3:27]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 104699822-Amino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazole

Product 1

HCID 156760462-Ethoxycarbonylamino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazoleYield 635.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 2-amino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazole (5.00 g, 1.68 mmol) in tetrahydrofuran (150 ml) was added ethyl chloroformate (1.82 g, 16.8 mmol) and triethylamine (1.70 g, 16.8 mmol) and the mixture was stirred under reflux for 2 hr. After cooling, the reaction mixture was diluted with water, then extracted with ethyl acetate. The extracts were washed with 1N-HCl and water, dried, then evaporated under reduced pressure to a residue, which was chromatographed to afford 2-ethoxycarbonylamino-4-(1-(2-fluoro-4-biphenylyl)ethyl) thiazole (3.954 g, 64% yield): NMR(CDCl3)δ 1.31(t, 3H), 1.60(t, 3H), 4.25(m, 3H), 6.58(s, 1H), 6.95-7.58(m, 8H) ppm; IR(nujol) 3280, 1720, 1290, 1230, 1080 cm-1.

Workup

  1. temperatureunder reflux for 2 hr
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with 1N-HCl and water
  5. customdried
  6. customevaporated under reduced pressure to a residue, which
  7. customwas chromatographed

Sources & evidence

ORD record
ord-a16cc26066764410b036a0e3f22c7cf0
Source dataset
uspto-grants-1991_11
Patent number
US05066666

Reaction notes

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