Dipropylamine → 7-((Dipropylamino)methyl)-N-mesityl-1,3-benzothiazol-2-amine

HRID 2235525Notes

Reaction equation

HRID 2235525 reaction equation
Br[CH2:2][C:3]1[C:11]2[S:10][C:9]([NH:12][C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])=[N:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:28]([NH:31][CH2:32][CH2:33][CH3:34])[CH2:29][CH3:30]>C(#N)C.ClCCl>[CH2:28]([N:31]([CH2:2][C:3]1[C:11]2[S:10][C:9]([NH:12][C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])=[N:8][C:7]=2[CH:6]=[CH:5][CH:4]=1)[CH2:32][CH2:33][CH3:34])[CH2:29][CH3:30]

Participants

6

Reactant 3

HCID 8902DipropylamineHCID 11430Potassium CarbonateHCID 860491237-(Bromomethyl)-N-mesityl-1,3-benzothiazol-2-amine

Product 1

HCID 588965287-((Dipropylamino)methyl)-N-mesityl-1,3-benzothiazol-2-amineYield 59%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

To 0.045 g (0.12 mmol) of 7-(bromomethyl)-N-mesityl-1,3-benzothiazol-2-amine in 0.5 mL of acetonitrile and 2 mL of dichloromethane was added 0.086 g (0.62 mmol) of potassium carbonate and 85 μl, (0.62 mmol) of dipropylamine. The reaction was stirred for 40 min, diluted with dichloromethane and filtered. The filtrate was concentrated and purified by flash chromatography eluting with a 25% ethyl acetate/hexanes mixture to give 0.027 g (57%) of the title compound as a light yellow powder.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. custompurified by flash chromatography
  4. washeluting with a 25% ethyl acetate/hexanes mixture

Sources & evidence

ORD record
ord-870ef0b6fab14944bf7c52fd7f376179
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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