Triethylamine → Maleic Acid

HRID 1902316Notes

Reaction equation

HRID 1902316 reaction equation
Cl.Cl.[CH3:3][C:4]1[N:5]=[CH:6][NH:7][C:8]=1[CH2:9][S:10][CH2:11][CH2:12][NH2:13].C(N(CC)CC)C.[F:21][C:22]([F:41])([F:40])[CH2:23][N:24]=[C:25]([NH2:39])[NH:26][C:27]1[S:28][CH:29]=[C:30]([CH2:32][CH2:33][CH2:34][CH2:35][N:36]=[C:37]=[S:38])[N:31]=1.[C:42]([OH:49])(=[O:48])/[CH:43]=[CH:44]\[C:45]([OH:47])=[O:46]>O1CCCC1.CC(C)=O>[F:41][C:22]([F:21])([F:40])[CH2:23][N:24]=[C:25]([NH2:39])[NH:26][C:27]1[S:28][CH:29]=[C:30]([CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:37]([NH:13][CH2:12][CH2:11][S:10][CH2:9][C:8]2[NH:7][CH:6]=[N:5][C:4]=2[CH3:3])=[S:38])[N:31]=1.[C:42]([OH:49])(=[O:48])/[CH:43]=[CH:44]\[C:45]([OH:47])=[O:46]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 444266Maleic AcidHCID 30159992-(((5-Methyl-1H-imidazol-4-yl)methyl)thio)ethylamine dihydrochlorideHCID 212987892-[2-(2,2,2-Trifluoroethyl)guanidino]-(4-isothiocyanatobutyl)thiazole

Product 2

HCID 444266Maleic AcidHCID 178433324HCID 178433324, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-methyl-5-[(2-aminoethyl)thiomethyl]imidazole dihydrochloride (0.5 g.), triethylamine (1 ml.) and 2-[2-(2,2,2-trifluoroethyl)guanidino]-(4-isothiocyanatobutyl)thiazole (0.5 g.) in tetrahydrofuran (15 ml.) was allowed to stand at room temperature overnight. The solution then was filtered, and the filtrate evaporated to dryness. The residue was purified by preparative thin layer chromatography using ethyl acetate/methanol/ammonia 6:1:1 v/v/v as developing solvent. The appropriate band was isolated and further purified by preparative thin layer chromatography using methanol/chloroform/ammonia 15:85:1 v/v/v as developing solvent. The appropriate band after extraction and evaporation yielded a brown gum. This was treated in acetone with excess maleic acid to give 1-[4-(2-[2-(2,2,2-trifluoroethyl)-guanidino]thiazol-4-yl)butyl]-3-[2-([4-methylimidazol-5-yl]methylthio)ethyl]thiourea containing 2.25 equivalents of maleic acid. The n.m.r. spectrum in d6 dimethyl sulphoxide containing tetramethylsilane as internal standard (δ=0) included the following resonances (δ):-1.5 (multiplet, 4H); 2.25 (singlet, 3H); 2.5 (multiplet, 4H); 3.3 (multiplet, 4H); 3.8 (singlet, 2H); 4.1 (quartet, 2H); 6.45 (singlet, 1H); 8.8 (singlet, 1H).

Workup

  1. filtrationThe solution then was filtered
  2. customthe filtrate evaporated to dryness
  3. customThe residue was purified by preparative thin layer chromatography
  4. customThe appropriate band was isolated
  5. customfurther purified by preparative thin layer chromatography
  6. extractionThe appropriate band after extraction and evaporation
  7. customyielded a brown gum

Sources & evidence

ORD record
ord-aceb126cd4d54991863115588e3eed19
Source dataset
uspto-grants-1982_12
Patent number
US04362728

Reaction notes

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