Triethylamine → HCID 178496794, compound

HRID 444010Notes

Reaction equation

HRID 444010 reaction equation
C(N(CC)CC)C.Cl.Cl.[NH:10]([C:14]1[S:15][CH:16]=[C:17]([CH2:19][S:20][CH2:21][CH2:22][NH2:23])[N:18]=1)[C:11]([NH2:13])=[NH:12].[CH3:24][O:25][C:26](OC)=[N:27][C:28]#[N:29]>CO>[NH:10]([C:14]1[S:15][CH:16]=[C:17]([CH2:19][S:20][CH2:21][CH2:22][NH:23][C:26](=[N:27][C:28]#[N:29])[O:25][CH3:24])[N:18]=1)[C:11]([NH2:13])=[NH:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90604Carbonimidic acid, N-cyano-, dimethyl esterHCID 178478806HCID 178478806, compound

Product 1

HCID 178496794HCID 178496794, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Triethylamine (2.02 g.) was added to a suspension of 2-guanidino-4-[(2-aminoethyl)thiomethyl]thiazole dihydrochloride (3.04 g.) in methanol (30 ml.) stirred at room temperature. Dimethyl (N-cyanoimido)carbonate (1.14 g.) was added and the mixture was stirred at room temperature for 3 hours and then evaporated under reduced pressure. The residue was extracted with ethyl acetate (35 ml.) and the solution was washed with water (25 ml., 10 ml.) then dried (magnesium sulphate) and evaporated under reduced pressure to give 2-guanidino-4-[2-(3-cyano-2-methylisoureido)ethylthiomethyl]thiazole (2.16 g.). The n.m.r. spectrum in CDCl3 /d6 dimethyl sulphoxide using tetramethylsilane as internal standard had the following resonances (δ); 7.7 (1H, very broad); 6.7 (4H, broad); 6.4 (1H, singlet); 3.8 (3H, singlet); 3.6 (2H, singlet); 3.4 (obscured by H2O); 2.7 (2H, broad triplet).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. customevaporated under reduced pressure
  3. extractionThe residue was extracted with ethyl acetate (35 ml.)
  4. washthe solution was washed with water (25 ml., 10 ml.)
  5. dry with materialthen dried (magnesium sulphate)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-df911ca1b65e429eb0eb86080bc705e8
Source dataset
uspto-grants-1981_04
Patent number
US04262126

Reaction notes

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