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

HRID 538886Notes

Reaction equation

HRID 538886 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 rug, 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 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+): 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. customdried
  5. filtrationover filtered
  6. concentrationconcentrated
  7. customThe crude product was purified by preparative TLC

Sources & evidence

ORD record
ord-cd7b110de2144c1796a2e9bcad9a8cd1
Source dataset
uspto-grants-2014_10
Patent number
US08865752B2

Reaction notes

Loading…