Dimethylformamide → N1-methyl-N1-(5-methylthiazol-2-yl)ethane-1,2-diamine

HRID 252932Notes

Reaction equation

HRID 252932 reaction equation
[CH3:1][NH:2][C:3]1[S:4][C:5]([CH3:8])=[CH:6][N:7]=1.[H-].[Na+].Br.Br[CH2:13][CH2:14][NH2:15].CN(C=O)C>C(Cl)Cl.CCO.O>[CH3:1][N:2]([C:3]1[S:4][C:5]([CH3:8])=[CH:6][N:7]=1)[CH2:13][CH2:14][NH2:15]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 817028N,5-dimethylthiazol-2-amineHCID 27742172-Bromoethylamine hydrobromide

Product 1

HCID 68418681N1-methyl-N1-(5-methylthiazol-2-yl)ethane-1,2-diamineYield 34%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

A mixture of 512 mg (4.0 mmol) of N,5-dimethylthiazol-2-amine, 352 mg (8.8 mmol, 60% strength in mineral oil) of sodium hydride and 2-bromoethylamine hydrobromide with DMF (10 ml) was stirred for 2 h at RT. The mixture was then poured into water and extracted with DCM. The organic phase was dried over MgSO4, filtered and evaporated under a vacuum. 232 mg (1.4 mmol, 34%) of N1-methyl-N1-(5-methylthiazol-2-yl)ethane-1,2-diamine were obtained by CC (DCM/EtOH/conc. aq. NH4—OH soln. 5:1:0.06) with the residue.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated under a vacuum

Sources & evidence

ORD record
ord-37c0593fef9e4bafaa49874b171b2676
Source dataset
uspto-grants-2011_01
Patent number
US07871999B2

Reaction notes

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