Methanol → HCID 67385454, compound

HRID 1410283Notes

Reaction equation

HRID 1410283 reaction equation
[CH2:1]([N:3]([CH2:21][CH3:22])[CH2:4][CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[CH:14][C:15]([OH:17])=[O:16])=[CH:9][C:8]=1[N+:18]([O-:20])=[O:19])[CH3:2].S(=O)(=O)(O)O.[CH3:28]O>>[CH2:21]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]([O:17][CH3:28])=[O:16])=[CH:9][C:8]=1[N+:18]([O-:20])=[O:19])[CH3:22]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 67385288HCID 67385288, compound

Product 1

HCID 67385454HCID 67385454, compound

Procedure

3-(4-(2-(Diethylamino)ethylthio)-3-nitrophenyl)acrylic acid (1.74 g, 5.4 mmol) was suspended in methanol (25 mL) under stirring. To this solution, concentrated sulfuric acid (1.0 mL) was added. The resulted solution was heated to reflux for 19 hours. Cooling it to room temperature and the solvent was removed under reduced pressure. 100 ml water was added to dissolve the resulted residue. Cooling it with an ice-bath and adjusting the pH value to 9.0 using ammonia under stirring. (E)-methyl 3-(4-(2-(diethylamino)ethylthio)-3-nitrophenyl)acrylate was obtained as yellow solid. TLC: Rf=0.75 (DCM:MeOH=9:1); MP: 57.4° C.-59.1° C. HPLC: 92.0%; tR=9.74 min (LC/PDA: Diamonsil C18 5μ 150×4.6 mm, flow rate: 1.0 mL/min, grade: 10-100% B, 20 minutes: mobile phase A: water; mobile phase B: acetonitrile; UV254); IR (cm−1): 2967, 2926, 1720, 1639, 1604, 918. 1HNMR (400 MHz, CDCl3) δ: 8.36 (1H, s), 7.70 (1H, d, J=1.6 Hz), 7.69 (1H, d, J=16 Hz), 7.50 (1H, d, J=8 Hz), 7.27 (1H, s), 6.51 (1H, d, J=16 Hz), 3.83 (3H, s), 3.12 (2H, t, J=8 Hz); 2.83 (2H, t, J=8 Hz); 2.64 (4H, q, J=7.2 Hz), 1.07 (6H, t, J=7.2 Hz). MS (m/z): 339 (MH)+.

Workup

  1. temperatureThe resulted solution was heated
  2. temperatureto reflux for 19 hours
  3. customthe solvent was removed under reduced pressure
  4. addition100 ml water was added
  5. dissolutionto dissolve the resulted residue
  6. temperatureCooling it with an ice-bath
  7. stirringunder stirring

Sources & evidence

ORD record
ord-66c72b5cca5740aeaae4fd74fd766e70
Source dataset
uspto-grants-2014_12
Patent number
US08921424B2

Reaction notes

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