Ethanol → HCID 11141327, compound

HRID 1856831Notes

Reaction equation

HRID 1856831 reaction equation
C(O[C:4]([C:6]1[S:7][C:8]([S:18][CH3:19])=[C:9]2[C:14](=[O:15])[CH2:13][C:12]([CH3:17])([CH3:16])[CH2:11][C:10]=12)=[NH:5])C.[CH3:20][NH:21][NH2:22].[CH2:23](O)C>>[CH3:16][C:12]1([CH3:17])[CH2:11][C:10]2=[C:6]([C:4]3[N:5]=[CH:20][N:21]([CH3:23])[N:22]=3)[S:7][C:8]([S:18][CH3:19])=[C:9]2[C:14](=[O:15])[CH2:13]1

Participants

4

Reactant 3

HCID 702EthanolHCID 6061MethylhydrazineHCID 11823817HCID 11823817, compound

Product 1

HCID 11141327HCID 11141327, compoundYield 15%

Conditions

Temperature
50 °C

Procedure

6,6-Dimethyl-3-methylthio-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one-1-carboximidic acid ethyl ester (1.0 g, 3.37 mmol) was dissolved in ethanol (60 mL) and methyl hydrazine (0.16 g, 3.37 mmol) was added. The solution was heated at 50° C. for 7 h then evaporated to dryness and the residue was taken up in formic acid (20 mL). The solution was heated at 100° C. for 16 h then evaporated to dryness. The residue was dissolved in DCM and washed with saturated K2CO3 solution, then evaporated to dryness. The crude product was chromatographed on silica gel, eluting with ethyl acetate to yield the title compound as a yellow solid (0.15 g, 15%). mp 146-148° C. C14H17N3OS2 requires: C, 54.70; H, 5.77; N, 13.27%. Found: C, 54.55; H, 5.46; N, 13.27%. 1H NMR (250 MHz, CDCl3) δ1.05 (6H, s), 2.44 (2H, s), 2.63 (3H, s), 2.74 (2H, s), 3.96 (3H, s), 7.98 (1H, s). MS (ES+) 308 (M+1).

Workup

  1. customthen evaporated to dryness
  2. temperatureThe solution was heated at 100° C. for 16 h
  3. customthen evaporated to dryness
  4. dissolutionThe residue was dissolved in DCM
  5. washwashed with saturated K2CO3 solution
  6. customevaporated to dryness
  7. customThe crude product was chromatographed on silica gel
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-c435f0ad98d5443bb2f2bf297de408cf
Source dataset
uspto-grants-2000_11
Patent number
US06143773

Reaction notes

Loading…