Carbonocyanidic acid, methyl ester → HCID 23303087, compound

HRID 1489005Notes

Reaction equation

HRID 1489005 reaction equation
C([N:5]1[C:9](=O)[N:8]2[CH:11]=[CH:12][N:13]=[C:7]2[S:6]1)CCC.C([C:16]([O:18][CH3:19])=[O:17])#N>ClCCl>[CH3:19][O:18][C:16]([C:9]1[N:8]2[CH:11]=[CH:12][N:13]=[C:7]2[S:6][N:5]=1)=[O:17]

Participants

4

Reactant 2

HCID 28660Carbonocyanidic acid, methyl esterHCID 11171593HCID 11171593, compound

Product 1

HCID 23303087HCID 23303087, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution of 2-butylimidazo[1,2-d]-1,2,4-thiadiazole-3(2H)-one (2.95 g, 15.0 mmole) in 25 mL dichloromethane, methyl cyanoformate (2.54 g, 30 mmole) was added dropwise and the mixture was stirred for 16 h at room temperature. The precipitate was filtered and subsequently washed with dichloromethane to give 2.18 g (80%) of 3-(methoxycarbonyl)imidazo[1,2-d]-1,2,4-thiadiazole as colourless crystals: mp 164.5°-165° C.; 1H NMR (CDCl3) δ8.13 (s, 1H), 7.51 (s, 1H), 4.11 (s, 3H) ppm; IR (KBr) δ3440, 1737, 1527, 1253, 1071 cm-1. Anal. Calcd for C6H5N3 O2S: C, 39.34; H, 2.75; N, 22.94. Found: C, 39.41; H, 2.51; N, 22.94.

Workup

  1. filtrationThe precipitate was filtered
  2. washsubsequently washed with dichloromethane

Sources & evidence

ORD record
ord-9a8215c948094146b5ce3f46e944da8a
Source dataset
uspto-grants-1997_10
Patent number
US05677302

Reaction notes

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