HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

2-Chloro-5-aminomethylthiazole → 1-(1-Chloroethoxycarbonyl)-3-(2-chloro-5-thiazolylmethyl)-1-methyl-2-nitroguanidine

HRID 1657032
Notes
Print preview

Reaction equation

HRID 1657032 reaction equation
[Cl:1][CH:2]([O:4][C:5]([N:7]([CH3:15])[C:8](=[N:11][N+:12]([O-:14])=[O:13])SC)=[O:6])[CH3:3].[Cl:16][C:17]1[S:18][C:19]([CH2:22][NH2:23])=[CH:20][N:21]=1>C(Cl)(Cl)Cl>[Cl:1][CH:2]([O:4][C:5]([N:7]([CH3:15])[C:8]([NH:23][CH2:22][C:19]1[S:18][C:17]([Cl:16])=[N:21][CH:20]=1)=[N:11][N+:12]([O-:14])=[O:13])=[O:6])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 101541292-Chloro-5-aminomethylthiazoleHCID 73653905N-(1-chloroethoxycarbonyl)-S,N-dimethyl-N'-nitroisothiourea

Product 1

HCID 1363315011-(1-Chloroethoxycarbonyl)-3-(2-chloro-5-thiazolylmethyl)-1-methyl-2-nitroguanidineYield 38.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a stirred solution of N-(1-chloroethoxycarbonyl)-S,N-dimethyl-N'-nitroisothiourea (6.50 g) in CHCl3 (15 ml) was added a solution of 2-chloro-5-thiazolylmethylamine (3.78 g) in CHCl3 (5 ml) dropwise below -20° C. over 20 minutes. After stirring at -20° C. for 30 minutes, insolubles were removed by filtration and the filtrate was concentrated in vacuo. The residue was applied to column chromatography on silica gel. The column was eluted with hexane-AcOEt (1:1) to afford 3.50 g of 1-(1-chloroethoxycarbonyl)-3-(2-chloro-5-thiazolylmethyl)-1-methyl-2-nitroguanidine (Compound No. 12) as an orange oil.

Workup

  1. custominsolubles were removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. washThe column was eluted with hexane-AcOEt (1:1)

Sources & evidence

ORD record
ord-aed818bb104d487aaca0b5a48d7700ef
Source dataset
uspto-grants-1993_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05256679

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes