Sodium Hydroxide → 1-(2-Chloro-5-thiazolylmethyl)-3,3-dimethyl-l-methanesulphonyl-2-nitroguanidine

HRID 1657034Notes

Reaction equation

HRID 1657034 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH2:7][NH:8][C:9]([N:14]([CH3:16])[CH3:15])=[N:10][N+:11]([O-:13])=[O:12])=[CH:5][N:6]=1.[OH-].[Na+].[CH3:19][S:20](Cl)(=[O:22])=[O:21]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:1][C:2]1[S:3][C:4]([CH2:7][N:8]([S:20]([CH3:19])(=[O:22])=[O:21])[C:9]([N:14]([CH3:16])[CH3:15])=[N:10][N+:11]([O-:13])=[O:12])=[CH:5][N:6]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 136218199N-(2-chloro-5-thiazolylmethyl)-N',N'-dimethyl-N"-nitroguanidine

Product 1

HCID 542831511-(2-Chloro-5-thiazolylmethyl)-3,3-dimethyl-l-methanesulphonyl-2-nitroguanidineYield 41.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-chloro-5-thiazolylmethyl)-3,3- dimethyl-2-nitroguanidine (0.300 g) in an aqueous NaOH solution (NaOH (0.319 g) and water (10 ml)) were added CH2Cl2 (10 ml) and 4-dimethylaminopyridine (0.013 g). To the mixture was added methanesulphonyl chloride (0.391 g) dropwise at room temperature under stirring. After stirring for 30 minutes, the mixture was partitioned. The organic layer was dried over MgSO, and concentrated in vacuo. The resulting residue was applied to column chromatography on silica gel. The column was eluted with hexane-AcOEt (1:1) to afford 0.160 g of 1-(2-chloro-5-thiazolylmethyl)-3,3-dimethyl-l-methanesulphonyl-2-nitroguanidine (Compound No. 28) as a pale yellow crystal, m.p. 82°-86° C.

Workup

  1. stirringAfter stirring for 30 minutes
  2. customthe mixture was partitioned
  3. dry with materialThe organic layer was dried over MgSO
  4. concentrationconcentrated in vacuo
  5. washThe column was eluted with hexane-AcOEt (1:1)

Sources & evidence

ORD record
ord-3af5a110d2d0447ab9064add5c3f9445
Source dataset
uspto-grants-1993_10
Patent number
US05256679

Reaction notes

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