Methylamine → HCID 178485205, compound

HRID 66583Notes

Reaction equation

HRID 66583 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH:10]2[CH2:15][CH2:14][CH2:13][CH:12]([NH:16][C:17](=[N:20][S:21]([CH3:24])(=[O:23])=[O:22])SC)[CH2:11]2)[N:9]=1)[C:2]([NH2:4])=[NH:3].[CH3:25][NH2:26].[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]\[C:30]([OH:32])=[O:31]>CO.C(Cl)(Cl)Cl.C(O)C.CO.CC(C)=O.CCOCC>[OH2:22].[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]\[C:30]([OH:32])=[O:31].[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH:10]2[CH2:15][CH2:14][CH2:13][CH:12]([NH:16][C:17]([NH:26][CH3:25])=[N:20][S:21]([CH3:24])(=[O:22])=[O:23])[CH2:11]2)[N:9]=1)[C:2]([NH2:4])=[NH:3]

Participants

9

Reactant 3

HCID 6329MethylamineHCID 444266Maleic AcidHCID 178504068HCID 178504068, compound

Product 1

HCID 178485205HCID 178485205, compound

Reagents, catalysts & solvents 5

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 21584188Chloroform methanolSolvent

Procedure

A solution of 2-guanidino-4-[3-(3-methylsulphonyl-2-methylisothioureido)cyclohexyl]thiazole (0.25 g.) in methanol/chloroform 50:50 v/v (15 ml.) was treated with 20 ml. of 33% w/v methylamine in ethanol and the mixture allowed to stand at room temperature overnight. Evaporation of the solvent gave a gum which was dissolved in methanol (1 ml.) and to this solution was added an excess of maleic acid in acetone. The resulting solution was diluted with ether until crystallisation occurred, giving 2-guanidino-4-[3-(2-methylsulphonyl-3-methylguanidino)cyclohexyl]-thiazole hydrogen maleate monohydrate, m.p. 184°-187° (decomp).

Workup

  1. customEvaporation of the solvent
  2. customgave a gum which

Sources & evidence

ORD record
ord-8c3dbb999cf845789388e00f453c7701
Source dataset
uspto-grants-1982_08
Patent number
US04342765

Reaction notes

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