Ammonia → HCID 178422924, compound

HRID 1926238Notes

Reaction equation

HRID 1926238 reaction equation
S(=O)(=O)(O)O.CO[CH:8](OC)[C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)=[O:10].N>>[CH3:19][C:16]1[CH:15]=[C:14]2[C:13](=[CH:18][CH:17]=1)[CH:12]=[N:11][C:9]([OH:10])=[CH:8]2

Participants

4

Reactant 3

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 214193642,2-Dimethoxy-N-[(4-methylphenyl)methyl]acetamide

Product 1

HCID 178422924HCID 178422924, compound

Procedure

Concentrated sulfuric acid (18 M; 11.0 mL) was added to 2,2-dimethoxy-N-(4-methylbenzyl)-acetamide (1.95 g, 8.73 mmol) at ambient temperature, and the solution was stirred overnight at ambient temperature. The reaction mixture was added to ≈100 mL of ice, and the pH of the mixture was adjusted to ≈5 with concentrated aq. NH3 solution. The yellow precipitate was filtered off, washed with water, and dried in vacuo overnight to give the title compound as yellow solid. It was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6): δ=8.79 (s, 1H), 7.81 (d, J=8.4 Hz, 1H), 7.44 (s, 1H), 7.14 (dd, J=1.6, 8.4 Hz, 1H), 6.76 (s, 1H), 2.42 (s, 3H); —OH not apparent. MS(ES+): m/z=160.25 (100) [MH+], 142.13 (12) [MH+—H2O]. HPLC: tR=2.15 min (polar—5 min, ZQ2), 2.25 min (polar—5 min, ZQ3).

Workup

  1. filtrationThe yellow precipitate was filtered off
  2. washwashed with water
  3. customdried in vacuo overnight

Sources & evidence

ORD record
ord-aeb8a40a3f8e4a09ae15f31ae1df23f5
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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