Hydrochloric Acid → HCID 136331502, compound

HRID 1657035Notes

Reaction equation

HRID 1657035 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH2:7][N:8]([C:16](=[O:19])[CH2:17][CH3:18])[C:9](=[N:12][N+:13]([O-:15])=[O:14])SC)=[CH:5][N:6]=1.[CH3:20][NH2:21].CO.Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[S:3][C:4]([CH2:7][N:8]([C:16](=[O:19])[CH2:17][CH3:18])[C:9]([NH:21][CH3:20])=[N:12][N+:13]([O-:15])=[O:14])=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 57454252Monomethylamine methanolHCID 70203986HCID 70203986, compound

Product 1

HCID 136331502HCID 136331502, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of N-(2-chloro-5-thiazolylmethyl)-S-methyl-N'-nitro-N-propionylisothiourea (310 mg) in toluene (5 ml) was added 40% methylamine-methanol solution (75 mg) below -10° C. and the mixture was stirred at the same temperature for 3 hours. After addition of 2N hydrochloric acid (5 ml) under ice-cooling, the mixture was extracted with AcOEt (10 ml). The organic layer was washed with an aqueous saturated sodium bicarbonate solution, dried over MgSO4 and concentrated in vacuo. The resulting residue was applied to column chromatography on silica gel. The column was eluted with AcOEt. The fractions containing the desired compound were concentrated and the residue was dissolved in toluene. Crystallization by addition of n-hexane gave 120 mg of 1-(2-chloro-5-thiazolylmethyl)-3-methyl-2-nitro-1-propionylguanidine (Compound No. 32) as a white crystal, m.p. 89°-90° C.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with AcOEt (10 ml)
  3. washThe organic layer was washed with an aqueous saturated sodium bicarbonate solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. washThe column was eluted with AcOEt
  7. additionThe fractions containing the desired compound
  8. concentrationwere concentrated
  9. dissolutionthe residue was dissolved in toluene
  10. customCrystallization
  11. additionby addition of n-hexane

Sources & evidence

ORD record
ord-a5bf0bc244434210a3860f13e9a1b20b
Source dataset
uspto-grants-1993_10
Patent number
US05256679

Reaction notes

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