Maleic Acid → Maleic Acid

HRID 364313Notes

Reaction equation

HRID 364313 reaction equation
[F:1][C:2]([F:19])([F:18])[CH2:3][N:4]=[C:5]([NH2:17])[NH:6][C:7]1[S:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])[N:11]=1.[F:20][C:21]([F:40])([F:39])[CH2:22][N:23]=[C:24]([NH2:38])[NH:25][C:26]1[S:27][CH:28]=[C:29]([CH2:31][CH2:32][CH2:33][CH2:34][N:35]=C=S)[N:30]=1.[C:41]([OH:48])(=[O:47])/[CH:42]=[CH:43]\[C:44]([OH:46])=[O:45]>CO.CC(C)=O>[F:19][C:2]([F:1])([F:18])[CH2:3][N:4]=[C:5]([NH2:17])[NH:6][C:7]1[S:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][NH:6][C:7]([NH:11][NH:35][CH2:34][CH2:33][CH2:32][CH2:31][C:29]2[N:30]=[C:26]([NH:25][C:24]([NH2:38])=[N:23][CH2:22][C:21]([F:20])([F:39])[F:40])[S:27][CH:28]=2)=[S:8])[N:11]=1.[C:41]([OH:48])(=[O:47])/[CH:42]=[CH:43]\[C:44]([OH:46])=[O:45]

Participants

7

Reactant 3

HCID 444266Maleic AcidHCID 212987102-[2-(2,2,2-Trifluoroethyl)-guanidino]-4-(4-aminobutyl)thiazoleHCID 212987892-[2-(2,2,2-Trifluoroethyl)guanidino]-(4-isothiocyanatobutyl)thiazole

Product 2

HCID 444266Maleic AcidHCID 540273311,3-Di[4-(2-[2-(2,2,2-trifluoroethyl)-guanidino]thiazol-4-yl)butylamino)thiourea

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

A mixture of 2-[2-(2,2,2-trifluoroethyl)guanidino]-4-(4-aminobutyl)thiazole (0.12 g.) and 2-[2-(2,2,2-trifluoroethyl)guanidino]-4-[4-isothiocyanatobutyl]thiazole (0.12 g.) in methanol (3 ml.) was allowed to stand at room temperature overnight. The mixture was then evaporated to dryness and purified by preparative thin layer chromatography using methanol/chloroform/ammonia 85:15:1 v/v/v as developing solvent. The appropriate band was extracted with chloroform/ethanol 1:1 v/v (200 ml.) and the resulting solution evaporated to give a brown gum. This was treated in acetone with excess maleic acid to give 1,3-di[4-(2-[2-(2,2,2-trifluoroethyl)guanidino]thiazol-4-yl)butylamino)thiourea containing 2.25 equivalents of maleic acid. The n.m.r. spectrum in d6 dimethylsulphoxide containing tetramethylsilane as internal standard (δ=0) included the following resonances (δ): 1.5 (multiplet, 8H); 3.3 (multiplet, 4H); 4.1 (quartet, 4H); 6.5 (singlet, 2H).

Workup

  1. customThe mixture was then evaporated to dryness
  2. custompurified by preparative thin layer chromatography
  3. extractionThe appropriate band was extracted with chloroform/ethanol 1:1 v/v (200 ml.)
  4. customthe resulting solution evaporated
  5. customto give a brown gum

Sources & evidence

ORD record
ord-3a7394fd2a3e4f9f88fd0382b126bd99
Source dataset
uspto-grants-1986_08
Patent number
US04604465

Reaction notes

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