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Diisopropylamine → N-methyl-N'-(4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazol-2-yl)thiourea

HRID 974054
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HRID 974054 반응식
C([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.[NH2:21][C:22]1[S:23][CH:24]=[C:25]([CH:27]([C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[C:31]([F:41])[CH:30]=2)[CH3:28])[N:26]=1.[CH3:42][N:43]=[C:44]=[S:45]>O1CCCC1>[CH3:42][NH:43][C:44]([NH:21][C:22]1[S:23][CH:24]=[C:25]([CH:27]([C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[C:31]([F:41])[CH:30]=2)[CH3:28])[N:26]=1)=[S:45]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 7912DiisopropylamineHCID 11167Methyl isothiocyanateHCID 2724682Lithium diisopropylamideHCID 104699822-Amino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazoleHCID 178418339Butyllithium

생성물 1

HCID 15676068N-methyl-N'-(4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazol-2-yl)thiourea수율 37.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To lithium diisopropylamide in tetrahydrofuran prepared with diisopropylamine (0.187 g, 1.85 mmol) and n-butyllithium (1.9 mmol) was added 2-amino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazole (0.50 g, 1.68 mmol) in tetrahydrofuran at -70° C. After the mixture was stirred for 20 min, methylisothiocyanate (0.131 g, 1.8 mmol) in tetrahydrofuran was added to the mixture. After the mixture was stirred at room temperature for 3.5 h, the mixture was evaporated under reduced pressure to a residue, which was extracted with chloroform. The extracts were washed with water, dried over, and evaporated under reduced pressure to a residue, which was chromatographed and recrystallized to afford N-methyl-N'-(4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazol-2-yl)thiourea (0.233 g, 35% yield) as crystalline material: mp 180.5°-181.0° C.

후처리

  1. stirringAfter the mixture was stirred at room temperature for 3.5 h
  2. customthe mixture was evaporated under reduced pressure to a residue, which
  3. extractionwas extracted with chloroform
  4. washThe extracts were washed with water
  5. customdried over, and
  6. customevaporated under reduced pressure to a residue, which
  7. customwas chromatographed
  8. customrecrystallized

출처 및 근거

ORD 기록
ord-5a9e03d33fb94f99a0834fbff72218cf
출처 데이터셋
uspto-grants-1991_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05066666

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