Dimethyl Sulfate → HCID 20503824, compound

HRID 1702456Notes

Reaction equation

HRID 1702456 reaction equation
C([NH:4][C:5]1[CH:11]=[CH:10]C(=O)[C:8]([OH:13])=[CH:7][CH:6]=1)(=O)C.[C:14](=[O:17])([O-])[O-].[K+].[K+].S(OC)(O[CH3:24])(=O)=O.C[C:28](=[O:31])[CH2:29][CH3:30]>>[CH3:24][O:13][C:8]1[C:14](=[O:17])[CH:10]=[CH:11][C:5]([NH:4][C:28](=[O:31])[CH2:29][CH3:30])=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6497Dimethyl SulfateHCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 257607NSC85774

Product 1

HCID 20503824HCID 20503824, compound

Procedure

A stirred mixture of 5-(acetylamino)-2-hydroxy-2,4,6-cycloheptatrien-1-one (148 g), described by T. Nozoe et al., Proc. Japan Acad., 27, 188 (1951), anhydrous potassium carbonate (300 g), dimethyl sulfate (300 g) and 2-butanone (3 l) was heated at reflux for 20 hr. The hot mixture was filtered and the filtrate was set aside. The collected solid was mixed with fresh quantities of potassium carbonate (300 g), dimethyl sulfate (300 g) and 2-butanone (3 l). The resulting mixture was heated at reflux for 20 hr and filtered while still hot. The combined filtrates were evaporated to dryness. The residue was subjected to chromatography on silica gel using chloroform:methanol (19:1) as the eluant. The pure fractions were pooled giving 2-methoxy-5-(N-methylacetylamino)-2,4,6-cycloheptatrien-1-one (56 g); mp 116°-118° C.; nmr (DMSO-d6) δ1.45(s, 3H), 3.2 (s, 3H), 3.95 (s, 3H), 6.5-7.2 (m, 4H), uv λ max (MeOH) 324 nm (ε10,835), 230 (22,940).

Workup

  1. temperatureat reflux for 20 hr
  2. filtrationThe hot mixture was filtered
  3. additionThe collected solid was mixed with fresh quantities of potassium carbonate (300 g), dimethyl sulfate (300 g) and 2-butanone (3 l)
  4. temperatureThe resulting mixture was heated
  5. temperatureat reflux for 20 hr
  6. filtrationfiltered while still hot
  7. customThe combined filtrates were evaporated to dryness

Sources & evidence

ORD record
ord-7762f887208147738eea3772118e9e9a
Source dataset
uspto-grants-1983_04
Patent number
US04381304

Reaction notes

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