Hydrochloric Acid → HCID 53745834, compound

HRID 1657031Notes

Reaction equation

HRID 1657031 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH2:7][N:8]([C:16]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:17])[C:9]([NH:14][CH3:15])=[N:10][N+:11]([O-:13])=[O:12])=[CH:5][N:6]=1.N1C=CC=CC=1.[C:31](Cl)(=[O:39])[O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.Cl>CC#N.O.C(Cl)(Cl)Cl>[Cl:1][C:2]1[S:3][C:4]([CH2:7][N:8]([C:16]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:17])[C:9]([N:14]([C:31]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:39])[CH3:15])=[N:10][N+:11]([O-:13])=[O:12])=[CH:5][N:6]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1049Pyridine2×HCID 15891Phenyl chloroformate3×HCID 136331500HCID 136331500, compound

Product 1

HCID 53745834HCID 53745834, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent2×

Procedure

A mixture of 1-(2-chloro-5-thiazolylmethyl)-1- phenoxycarbonyl-3-methyl-2-nitroguanidine (Compound No. 6), CH3CN (15 ml) and pyridine (0.55 ml) was cooled to 3°-C. followed by addition of phenyl chlorocarbonate (1.7 ml) in CH3CN (3 ml) below 8° C. over 2 minutes under stirring. After stirring at the same temperature for 1 hour and 25 minutes and then at room temperature for 1 hour, pyridine (0.55 ml) and phenyl chlorocarbonate (1.7 ml) was added to the mixture followed by stirring at room temperature for 1 hour and 15 minutes and at 40° C. for 2 hours. Additional phenyl chlorocarbonate (1.7 ml) was added to the mixture which was stirred for 20 minutes. To the reaction mixture was added CHCl3 (30 ml) and then a mixture of conc. hydrochloric acid (2 ml) and water (8 ml). The reaction mixture was partitioned and the aqueous layer was extracted with CHCl3 (20 ml×3). The combined organic layers were dried over MgSO4 and concentrated in vacuo. The resulting residue was applied to column chromatography on silica gel. The column was eluted with hexane-AcOEt (3:2) to afford 0.7 g of 1-(2-chloro-5-thiazolylmethyl)-I,3-diphenoxycarbonyl-3-methyl-2-nitroguanidine (Compound No. 2) as an oil.

Workup

  1. stirringAfter stirring at the same temperature for 1 hour and 25 minutes
  2. stirringby stirring at room temperature for 1 hour and 15 minutes and at 40° C. for 2 hours
  3. stirringwas stirred for 20 minutes
  4. customThe reaction mixture was partitioned
  5. extractionthe aqueous layer was extracted with CHCl3 (20 ml×3)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. washThe column was eluted with hexane-AcOEt (3:2)

Sources & evidence

ORD record
ord-a46cdce279774534a6a3cfad1c44d6d0
Source dataset
uspto-grants-1993_10
Patent number
US05256679

Reaction notes

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