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

HRID 2072724Notes

Reaction equation

HRID 2072724 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-7c24648f1e904f22a16d441795c17766
Source dataset
uspto-grants-1990_04
Patent number
US04914112

Reaction notes

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