Methylamine → HCID 21184439, compound

HRID 1385289Notes

Reaction equation

HRID 1385289 reaction equation
C(O[C:4](=[N:19][NH:20][CH:21]=O)[C:5]1[S:6][C:7]([S:17][CH3:18])=[C:8]2[C:13](=[O:14])[CH2:12][C:11]([CH3:16])([CH3:15])[CH2:10][C:9]=12)C.[CH3:23][NH2:24]>C(O)C>[CH3:15][C:11]1([CH3:16])[CH2:10][C:9]2=[C:5]([C:4]3[N:24]([CH3:23])[CH:21]=[N:20][N:19]=3)[S:6][C:7]([S:17][CH3:18])=[C:8]2[C:13](=[O:14])[CH2:12]1

Participants

4

Reactant 2

HCID 6329Methylamine2×HCID 70100453HCID 70100453, compound

Product 1

HCID 21184439HCID 21184439, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Formic acid[ethoxy-(6,6-dimethyl-3-methylthio-4-oxo-4,5,6,7-tetrahydrobenzo[c]thiophen-1-yl)methylene]hydrazide (150 mg, 0.49 mmol) was dissolved in a solution of methylamine in ethanol (30%, 10 mL) and the mixture heated at 60° C. More methylamine solution (10 mL) was added periodically over 8 h. The solution was evaporated to dryness and the residue purified by chromatographed on silica gel, eluting with methanol:dichloromethane (5:95). The title compound was obtained as a white powder (60 mg, 44%). mp 178-180° C. Found: C, 52.50; H, 5.43; N, 12.73%. C14H17N3OS2.0.8 (H2O) requires: C, 52.25; H, 5.83; N, 13.06%. 1HNMR (360 MHz, CDCl3)δ 1.05 (6H, s), 2.44 (2H, s), 2.62 (3H, s), 2.79 (2H, s), 3.75 (3H, s), 8.28 (1H, s). MS (ES+) 308 (M+1).

Workup

  1. customThe solution was evaporated to dryness
  2. customthe residue purified
  3. customby chromatographed on silica gel
  4. washeluting with methanol:dichloromethane (5:95)

Sources & evidence

ORD record
ord-a3b2b77f36364482a0f27138e37d8c59
Source dataset
uspto-grants-2001_07
Patent number
US06262103B1

Reaction notes

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