Imidazole → 4-Chloro-1-(cyclopropylmethyl)-5-[4-(iodomethyl)cyclohex-1-en-1-yl]-1H-benzotriazole

HRID 1626984ノート

反応式

HRID 1626984 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:25]I.[Cl:27][C:28]1[C:36]2[N:35]=[N:34][N:33]([CH2:37][CH:38]3[CH2:40][CH2:39]3)[C:32]=2[CH:31]=[CH:30][C:29]=1[C:41]1[CH2:46][CH2:45][CH:44]([CH2:47]O)[CH2:43][CH:42]=1>O1CCCC1>[Cl:27][C:28]1[C:36]2[N:35]=[N:34][N:33]([CH2:37][CH:38]3[CH2:40][CH2:39]3)[C:32]=2[CH:31]=[CH:30][C:29]=1[C:41]1[CH2:46][CH2:45][CH:44]([CH2:47][I:25])[CH2:43][CH:42]=1

参加物

6

反応物 4

HCID 795Imidazole3 回HCID 807Iodine3 回HCID 11776Triphenylphosphine3 回HCID 70977902{4-[4-Chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]cyclohex-3-en-1-yl}methanol

生成物 1

HCID 867137494-Chloro-1-(cyclopropylmethyl)-5-[4-(iodomethyl)cyclohex-1-en-1-yl]-1H-benzotriazole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒4 回

実験手順

To a tetrahydrofuran solution (2 mL) of triphenylphosphine (94 mg, 0.36 mmol, 1.1 equiv) was added imidazole (0.11 g, 1.6 mmol, 5 equiv) and iodine (86 mg, 0.34 mmol, 1.05 equiv). After stirring for 10 minutes, a tetrahydrofuran solution (1.5 mL) of {4-[4-chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]cyclohex-3-en-1-yl}methanol (Example 2, 0.10 g, 0.32 mmol) was added and the mixture was stirred for 1 hour. In a separate flask, a tetrahydrofuran solution (2 mL) was prepared containing triphenylphosphine (94 mg, 0.36 mmol, 1.1 equiv), imidazole (0.11 g, 1.6 mmol, 5 equiv) and iodine (86 mg, 0.34 mmol, 1.05 equiv), which was added to the reaction mixture after stirring for 10 minutes. After stirring for an additional 1 hour, an additional tetrahydrofuran solution (2 mL) containing triphenylphosphine (94 mg, 0.36 mmol, 1.1 equiv), imidazole (0.11 g, 1.6 mmol, 5 equiv) and iodine (86 mg, 0.34 mmol, 1.05 equiv) was added to the reaction mixture. After stirring for an additional 30 minutes, the mixture was purified by silica gel gradient chromatography (100:0 to 0:100; hexanes:ethly acetate), providing the titled compound as a light yellow oil.

後処理

  1. stirringthe mixture was stirred for 1 hour
  2. additionwas added to the reaction mixture
  3. stirringafter stirring for 10 minutes
  4. stirringAfter stirring for an additional 1 hour
  5. additionwas added to the reaction mixture
  6. stirringAfter stirring for an additional 30 minutes
  7. customthe mixture was purified by silica gel gradient chromatography (100:0 to 0:100; hexanes:ethly acetate)

出典と根拠

ORDレコード
ord-d7995481331540a08c9f82812cacf781
出典データセット
uspto-grants-2014_07
特許番号
US08785482B2

反応ノート

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