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

HRID 1059085Notes

Reaction equation

HRID 1059085 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH2:7][N:8]2CO[CH2:11][N:10](C)[C:9]2=[N:15][N+:16]([O-:18])=[O:17])=[CH:5][N:6]=1.[OH-].[Na+]>Cl>[Cl:1][C:2]1[S:3][C:4]([CH2:7][NH:8][C:9]([NH:10][CH3:11])=[N:15][N+:16]([O-:18])=[O:17])=[CH:5][N:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 107646n-(3-((2-Chlorothiazol-5-yl)methyl)-5-methyl-1,3,5-oxadiazinan-4-ylidene)nitramide

Product 1

HCID 135779804N-(2-chloro-5-thiazolylmethyl)-N'-methyl-N"-nitroguanidine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5.0 g of 5-(2-chlorothiazol-5-ylmethyl)-3-methyl4-nitroimino-perhydro-1,3,5-oxadiazine and 20 ml of concentrated hydrochloric acid is stirred for 2 hours at 80° C. The reaction mixture is cooled to 5° C., adjusted to a pH of about 5 with concentrated caustic soda solution and filtered. The filtering residue is mixed with diethyl ether/ethyl acetate 1:1 (v:v) and filtered again. The title compound is thus obtained.

Workup

  1. temperatureThe reaction mixture is cooled to 5° C.
  2. filtrationfiltered
  3. additionThe filtering residue is mixed with diethyl ether/ethyl acetate 1:1 (v:v)
  4. filtrationfiltered again

Sources & evidence

ORD record
ord-6033ebe4bb674791a690f17c331cc132
Source dataset
uspto-grants-2003_02
Patent number
US06518433B1

Reaction notes

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