Sulfuric Acid → HCID 178433434, compound

HRID 1926226Notes

Reaction equation

HRID 1926226 reaction equation
S(=O)(=O)(O)O.CO[CH:8](OC)[C:9]([NH:11][CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:13])=[O:10]>>[CH3:13][C:12]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=[C:9]([OH:10])[N:11]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 214193672,2-Dimethoxy-N-(1-phenylethyl)acetamide

Product 1

HCID 178433434HCID 178433434, compound

Conditions

Temperature
60 °C

Procedure

Concentrated sulfuric acid (18 M; 6.0 mL) was added to 2,2-dimethoxy-N-(1-phenylethyl)-acetamide (2.49 g, 11.2 mmol), and the resulting solution was stirred at 60° C. for 105 min. The reaction mixture was added to ≈100 mL of ice, and the yellow precipitate was filtered off. The pH of the filtrate was adjusted to 7-8 with NaHCO3 solution, the initial yellow solid was added, and the yellow precipitate was filtered off, washed with water, and dried in vacuo, giving the title compound as yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=10.68 (brs, 1H), 8.00 (dd, J=1.0, 8.6 Hz, 1H), 7.64 (d, J=8.4 Hz, 1H), 7.53 (dt, J=1.0, 8.0 Hz, 1H), 7.28 (dt, J=0.8, 8.0 Hz, 1H), 6.69 (s, 1H), 2.78 (s, 3H). MS(ES+): m/z=160.10 (100) [MH+]. HPLC: tR=2.13 min (polar—5 min, ZQ3).

Workup

  1. filtrationthe yellow precipitate was filtered off
  2. additionthe initial yellow solid was added
  3. filtrationthe yellow precipitate was filtered off
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-6ec65041e275411a864579f35a0372ae
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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