Dimethyl Sulfate → HCID 20311586, compound

HRID 2420366Notes

Reaction equation

HRID 2420366 reaction equation
[C:1]1([N:7]2[CH2:11][C:10]([NH2:12])=[N:9][C:8]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(OC)(O[CH3:18])(=O)=O>>[C:1]1([N:7]2[CH2:11][C:10](=[NH:12])[N:9]([CH3:18])[C:8]2=[O:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 6497Dimethyl SulfateHCID 20311575HCID 20311575, compound

Product 1

HCID 20311586HCID 20311586, compound

Conditions

Temperature
160 °C

Procedure

To 0.4 g. of 1-phenyl-4-amino-2-oxo-3-imidazoline was added 1 ml. of dimethyl sulfate. This mixture was slowly heated to 160° C., over a 45-minute period. The reaction mixture was put onto the vacuum pump and warmed to 90° C. to remove excess dimethyl sulfate. To the reaction was added 10 ml. of absolute alcohol giving a white solid. This material, 400 mg., was filtered and dried. This solid material was then added to water where it rapidly dissolved giving an acidic solution. This indicates the desired compound had precipitated from ethanol as the methyl sulfuric acid salt. Addition of 5N sodium hydroxide precipitated the desired product; after filtering and drying, 260 mg. (61%) of 1-phenyl-4-imino-3-methyl-2-oxoimidazolidine was obtained. This material was then recrystallized from acetone to give pure product, m.p. 156°-158° C. The mass spectrum of the compound gave a parent peak at m/e 189.

Workup

  1. temperaturewarmed to 90° C.
  2. customto remove excess dimethyl sulfate
  3. additionTo the reaction was added 10 ml
  4. filtration, was filtered
  5. customdried
  6. additionThis solid material was then added to water where it
  7. dissolutionrapidly dissolved
  8. customgiving an acidic solution

Sources & evidence

ORD record
ord-e694d794c3344f26947d1c90290ee596
Source dataset
uspto-grants-1978_08
Patent number
US04110445

Reaction notes

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