Ethanol → HCID 11141327, compound

HRID 1385295Notes

Reaction equation

HRID 1385295 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 CH2Cl2 and washed with saturated potassium carbonate solution, then evaporated to dryness. The crude product was purified by 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. Found: C, 54.55; H, 5.46; N, 13.27%. C14H17N3OS2 requires; C,54.70; H, 5.77; N, 13.27%. 1HNMR (250 MHz, CDCl3) δ 1.05 (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 CH2Cl2
  5. washwashed with saturated potassium carbonate solution
  6. customevaporated to dryness
  7. customThe crude product was purified
  8. customby chromatographed on silica gel
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-43e2e1bf9bbc4311a3fb8689431a666c
Source dataset
uspto-grants-2001_07
Patent number
US06262103B1

Reaction notes

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