Maleic Acid → Maleic Acid

HRID 1902315Notes

Reaction equation

HRID 1902315 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-66491e71d84d4b0c86d7fda9c685b062
Source dataset
uspto-grants-1982_12
Patent number
US04362728

Reaction notes

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