Benzylamine → HCID 59408775, compound

HRID 1188105Notes

Reaction equation

HRID 1188105 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:10]1[S:11][C:12]([C:15]([NH:17][C:18]2[S:19][C:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)=[CH:21][N:22]=2)=[O:16])=[CH:13][N:14]=1>CN(C=O)C.CCOC(C)=O>[CH2:1]([NH:8][C:10]1[S:11][C:12]([C:15]([NH:17][C:18]2[S:19][C:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)=[CH:21][N:22]=2)=[O:16])=[CH:13][N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 59408735HCID 59408735, compound

Product 1

HCID 59408775HCID 59408775, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzylamine (0.143 mL, 1.32 mmol) was added to a solution of 2-bromo-N-(5-p-tolylthiazol-2-yl)thiazole-5-carboxamide (250 mg, 0.66 mmol) in DMF (4 mL). The reaction mixture was stirred at reflux for 2 hrs. Then it was diluted with AcOEt and washed with water, dried with Na2SO4 and concentrated. The crude product was purified by precipitation (AcOEt/PE), yielding 2-(benzylamino)-N-(5-p-tolylthiazol-2-yl)thiazole-5-carboxamide (190 mg, 71%) as a solid.

Workup

  1. temperatureat reflux for 2 hrs
  2. washwashed with water
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by precipitation (AcOEt/PE)

Sources & evidence

ORD record
ord-b1cfb7b10940468c87902e904d28d3c9
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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