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

HRID 1894770Notes

Reaction equation

HRID 1894770 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-69d11e83d8a44ca7b7e5d1360b23a0ad
Source dataset
uspto-grants-2013_08
Patent number
US08513291B2

Reaction notes

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