Methyl isothiocyanate → HCID 178486121, compound

HRID 1155777Notes

Reaction equation

HRID 1155777 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[N:10]=[C:9]([NH:11][C:12]([NH2:14])=[NH:13])[S:8][N:7]=1.[CH3:15][N:16]=[C:17]=[S:18]>C(O)C>[CH3:15][NH:16][C:17](=[S:18])[NH:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[N:10]=[C:9]([NH:11][C:12]([NH2:14])=[NH:13])[S:8][N:7]=1

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 178512729HCID 178512729, compound

Product 1

HCID 178486121HCID 178486121, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-[(2-aminoethyl)thiomethyl]-5-guanidino-1,2,4-thiadiazole (0.914 g.) in ethanol (10 ml.) was heated under reflux with methyl isothiocyanate (0.288 g.) for 20 minutes and the resulting solution was chromatographed on nine preparative Merck 60 F-254 silica plates (30 cm.×30 cm.) developed with toluene/ethanol/ethyl acetate/ammonia (s.g. 0.88) 60:40:20:10 v/v/v/v. The bands with an Rf value of 0.6 were scraped off, extracted with ethanol and the extracts evaporated to a gum which crystallised on trituration with ethyl acetate to give 3-[2-(3-methylthioureido)ethylthiomethyl]-5-guanidino-1,2,4-thiadiazole. The n.m.r. spectrum in d6 dimethyl sulphoxide using tetramethylsilane as an internal standard (δ=0) had the following resonances (δ): 2.76 (2H, triplet); 2.82 (3 H, singlet); 3.35 (2H, multiplet); 3.71 (2H, singlet); 7.12 and 7.5 (6 H, multiplets).

Workup

  1. customthe resulting solution was chromatographed on nine preparative Merck 60 F-254 silica plates (30 cm.×30 cm.)
  2. extractionextracted with ethanol
  3. customthe extracts evaporated to a gum which
  4. customcrystallised on trituration with ethyl acetate

Sources & evidence

ORD record
ord-d2ccb124739c4504b2108f3bc888baf2
Source dataset
uspto-grants-1982_06
Patent number
US04332949

Reaction notes

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