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

HRID 974054
ノート
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反応式

HRID 974054 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5a9e03d33fb94f99a0834fbff72218cf
出典データセット
uspto-grants-1991_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05066666

反応ノート

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