2-Methyl-2-butene → 6-chloro-2-[2-cyano-2-({[4-(trifluoromethoxy)phenyl]carbonyl}amino)-propyl]-2H-benzotriazole-4-carboxylic acid

HRID 1257000ノート

反応式

HRID 1257000 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[O:31])[C:5]2[C:6]([CH:29]=1)=[N:7][N:8]([CH2:10][C:11]([NH:15][C:16](=[O:28])[C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1)([C:13]#[N:14])[CH3:12])[N:9]=2.CC(=CC)C.Cl[O-].[Na+].P([O-])(O)(O)=[O:41].[Na+]>C1COCC1.O.C(O)(C)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:30]([OH:41])=[O:31])[C:5]2[C:6]([CH:29]=1)=[N:7][N:8]([CH2:10][C:11]([C:13]#[N:14])([NH:15][C:16]([C:17]1[CH:18]=[CH:19][C:20]([O:23][C:24]([F:26])([F:25])[F:27])=[CH:21][CH:22]=1)=[O:28])[CH3:12])[N:9]=2

参加物

8

反応物 4

HCID 105532-Methyl-2-buteneHCID 23665760Sodium HypochloriteHCID 23672064Monosodium phosphateHCID 59327634N-[2-(6-Chloro-4-formyl-2H-benzotriazol-2-yl)-1-cyano-1-methylethyl]-4-trifluoromethoxybenzamide

生成物 1

HCID 666203556-chloro-2-[2-cyano-2-({[4-(trifluoromethoxy)phenyl]carbonyl}amino)-propyl]-2H-benzotriazole-4-carboxylic acid収率 87%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6386tert-Butanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of N-[2-(6-Chloro-4-formyl-2H-benzotriazol-2-yl)-1-cyano-1-methylethyl]-4-trifluoromethoxybenzamide (1.5 g) in a mixture of THF (25 mL), t-butanol (10 mL) and 2-methyl-2-butene was added dropwise the solution of sodium hypochlorite (0.9 g) and sodium dihydrogen phosphate (1.15 g) in water (20 mL). After 4 hour at room temperature, the mixture was concentrated under reduced pressure, diluted with water (50 mL) and acidified to pH 2 with normal HCl. The white solid was filtered and washed with water and dried under vacuum to give the title compound (1.35 g, 87%). MS (ES): M/Z [M+H]=468. 1H NMR: (400 MHz, DMSO-d6): 1.72 (s, 3H), 5.48-5.64 (m, 2H), 7.43 (d, J=8.2 Hz, 2H), 7.83 (d, J=2.0 Hz, 1H), 7.99 (d, J=8.8 Hz, 2H), 8.23 (d, J=1.8 Hz, 0H) and 9.41 (br. s., 1H). 19F NMR (376 MHz, DMSO-d6): −57.1 (s, 3F).

後処理

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additiondiluted with water (50 mL)
  3. filtrationThe white solid was filtered
  4. washwashed with water
  5. customdried under vacuum

出典と根拠

ORDレコード
ord-2f8d9a7495024c589c55955fc9d7259b
出典データセット
uspto-grants-2013_06
特許番号
US08461176B2

反応ノート

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