Sulfuric Acid → HCID 178431755, compound

HRID 1926230Notes

Reaction equation

HRID 1926230 reaction equation
S(=O)(=O)(O)O.[CH2:6]([NH:13][C:14](=[O:21])[C:15](OC)(OC)[CH3:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([O-])(O)=O.[Na+]>>[CH3:16][C:15]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[N:13][C:14]=1[OH:21]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 56980405N-benzyl-2,2-dimethoxypropionamide

Product 1

HCID 178431755HCID 178431755, compound

Conditions

Temperature
55 °C

Procedure

Concentrated sulfuric acid (18 M; 6.0 mL) was added to N-benzyl-2,2-dimethoxypropionamide (1.38 g, 6.18 mmol) at ambient temperature, and the solution was stirred at ambient temperature for 30 min and at 55° C. overnight. The reaction mixture was added to ≈100 mL of ice, and the pH of the yellow solution was adjusted to 7-8 with NaHCO3 solution. Small amounts of a brown solid that precipitated very soon during the addition (pH was still <2) were filtered off, and neutralization was continued. The yellow precipitate was filtered off, washed with water, and dried in vacuo, giving the title compound as yellow solid. It was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6): δ=10.6 (very brs, 1H), 8.74 (s, 1H), 7.91 (d, J=8.4 Hz, 1H), 7.83 (dd, J=0.8, 8.6 Hz, 1H), 7.61 (ddd, J=1.6, 6.4, 8.4 Hz, 1H), 7.31 (ddd, J=0.8, 6.4, 8.0 Hz, 1H), 2.37 (d, J=0.4 Hz, 3H). MS(ES+): m/z=160.10 (100) [MH+]. HPLC: tR=2.3 min (polar—5 min, ZQ3).

Workup

  1. customSmall amounts of a brown solid that precipitated very soon during the addition (pH
  2. filtrationwere filtered off
  3. filtrationThe yellow precipitate was filtered off
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-99d87449dac14618a6da23f5b64f78bf
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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