Dichloromethane → 1-[(4-iodophenyl)methyl]-2-(1-methylethyl)-4,5,6,7-tetrahydro-1H-benzimidazol-7-ol

HRID 1946546ノート

反応式

HRID 1946546 の反応式
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[C:14](=[O:18])[CH2:15][CH2:16][CH2:17][C:12]=3[N:11]=[C:10]2[CH:19]([CH3:21])[CH3:20])=[CH:4][CH:3]=1.ClCCl.[BH4-].[Na+]>CO>[I:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:13]3[CH:14]([OH:18])[CH2:15][CH2:16][CH2:17][C:12]=3[N:11]=[C:10]2[CH:19]([CH3:21])[CH3:20])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 584602073-[(4-iodophenyl)methyl]-2-(1-methylethyl)-3,5,6,7-tetrahydro-4H-benzimidazol-4-one

生成物 1

HCID 584601671-[(4-iodophenyl)methyl]-2-(1-methylethyl)-4,5,6,7-tetrahydro-1H-benzimidazol-7-ol収率 98.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To Intermediate 87 (6.65 g) in a 250 mL round-bottom flask under nitrogen in Methanol (20 mL) and Dichloromethane (DCM) (20 mL) was added sodium borohydride (1.276 g) in three portions (effervescence) and the mixture stirred at room temperature under nitrogen for 16 h. The solvent was removed under vacuum and the residue was partitioned between ethyl acetate and water. The aqueous layer extracted well with ethyl acetate. The combined organics were dried (hydrophobic frit), filtered and evaporated to give the title compound 6.6 g as a white solid. LC/MS MH+397, Rt 2.61 min (5 min run).

後処理

  1. customThe solvent was removed under vacuum
  2. customthe residue was partitioned between ethyl acetate and water
  3. extractionThe aqueous layer extracted well with ethyl acetate
  4. customThe combined organics were dried (hydrophobic frit)
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-ec762e1c374c4773b6f4fc2f0cebb631
出典データセット
uspto-grants-2013_03
特許番号
US08399444B2

反応ノート

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