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

HRID 974041
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인쇄 미리보기

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HRID 974041 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매
HCID 8028
Tetrahydrofuran
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a16cc26066764410b036a0e3f22c7cf0
출처 데이터셋
uspto-grants-1991_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05066666

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