Ammonium Hydroxide → 6-(2-ethyl-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-amine

HRID 1894770ノート

反応式

HRID 1894770 の反応式
[CH2:1]([CH:3]([CH2:17][CH3:18])[CH:4]([C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1)[CH3:2].[C:19]([S-:21])#[N:20].[K+].BrBr.[NH4+].[OH-]>CC(O)=O>[CH2:17]([CH:3]([CH2:1][CH3:2])[CH:4]([C:10]1[CH:11]=[CH:12][C:13]2[N:14]=[C:19]([NH2:20])[S:21][C:15]=2[CH:16]=1)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1)[CH3:18]

参加物

6

反応物 4

HCID 14923Ammonium HydroxideHCID 24408BromineHCID 516872Potassium thiocyanateHCID 866818974-(2-ethyl-1-(1H-imidazol-1-yl)butyl)aniline

生成物 1

HCID 547595316-(2-ethyl-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-amine

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

実験手順

A solution of 4-(2-ethyl-1-(1H-imidazol-1-yl)butyl)aniline (285 mg, 1.17 mmol) and KSCN (455 mg, 4.68 mmol) in AcOH (6 mL) was stirred until all dissolved at RT and then treated with Br2 (0.063 mL, 1.23 mmol) in AcOH (2 mL) added drop wise via syringe over 5 min. The reaction mixture was stirred overnight at RT. The reaction mixture was diluted with ice water and then basified with NH4OH (pH 12). The aqueous phase was extracted three times with DCM and the organic extracts were combined and dried over MgSO4, filtered and then concentrated. The crude product was purified by preparative TLC using 5% MeOH in DCM as eluent to afford to 6-(2-ethyl-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-amine as pale yellow solid. MS (ES+): m/z 301.27 (MH+).

後処理

  1. dissolutionall dissolved at RT
  2. additionadded drop wise via syringe over 5 min
  3. extractionThe aqueous phase was extracted three times with DCM
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by preparative TLC

出典と根拠

ORDレコード
ord-69d11e83d8a44ca7b7e5d1360b23a0ad
出典データセット
uspto-grants-2013_08
特許番号
US08513291B2

反応ノート

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