Sodium Hydroxide → N-(2-chloro-5-thiazolylmethyl)-N',N'-dimethyl-N"-nitroguanidine

HRID 1646675Notes

Reaction equation

HRID 1646675 reaction equation
[CH3:1][N:2]([CH3:9])[C:3]([NH:5][N+:6]([O-:8])=[O:7])=[NH:4].[OH-].[Na+].[Cl:12][C:13]1[S:14][C:15]([CH2:18]Cl)=[CH:16][N:17]=1>CN(C=O)C>[Cl:12][C:13]1[S:14][C:15]([CH2:18][NH:4][C:3]([N:2]([CH3:9])[CH3:1])=[N:5][N+:6]([O-:8])=[O:7])=[CH:16][N:17]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 27631792-Chloro-5-chloromethylthiazoleHCID 136047761N,N-Dimethyl-N'-nitroguanidine

Product 1

HCID 136218199N-(2-chloro-5-thiazolylmethyl)-N',N'-dimethyl-N"-nitroguanidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 13.0 g of N,N-dimethyl-N'-nitroguanidine, 5.90 g of powdery sodium hydroxide and 200 ml of dry DMF was dropwise added a solution of 2-chloro-5-(chloromethyl)thiazole in 15 ml of DMF over 2 hours while cooling with ice. The bath was removed, and stirring continued at room temperature for 13 hours followed by removal of the DMF by distillation under reduced pressure. To the residue was added 200 ml of acetonitrile followed by separation of insoluble materials by filtration on celite. The filtrate was purified by column chromatography (eluted with dichloromethane-acetonitrile 2:1-1:2). There was obtained 6.45 g of 1-(2-chloro-5-thiazolylmethyl)-3,3-dimethyl-2-nitroguanidine (reference compound No. 1), mp 155°-160° C. Crystallization from ethanol raised mp to 165.5°-166.5° C. NMR (DMSO-d6): 2.96(6H, s), 4.50(2H, d, J=5.8 Hz), 7.56(1H, s), 8.53(1H, br t, J=5.8 Hz).

Workup

  1. temperaturewhile cooling with ice
  2. customThe bath was removed
  3. customfollowed by removal of the DMF by distillation under reduced pressure
  4. additionTo the residue was added 200 ml of acetonitrile
  5. customfollowed by separation of insoluble materials by filtration on celite
  6. customThe filtrate was purified by column chromatography (eluted with dichloromethane-acetonitrile 2:1-1:2)

Sources & evidence

ORD record
ord-7813c8bc08ea4e98b0ce28feca43f1c1
Source dataset
uspto-grants-1993_01
Patent number
US05180833

Reaction notes

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