Methanol → HCID 178527782, compound

HRID 359920Notes

Reaction equation

HRID 359920 reaction equation
CO[C:3]1[C:4](=O)[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[NH2:11][C:12]([NH2:14])=[S:13].C[O-].[Na+].CO.CO>C(O)(=O)C>[SH:13][C:12]1[N:11]=[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=[C:3]2[N:14]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 165462-Methoxy-2,4,6-cycloheptatrien-1-oneHCID 2723790ThioureaHCID 23694274Sodium methanolate methanol

Product 1

HCID 178527782HCID 178527782, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In accordance with the method described in Journal of the Americal Chemical Society, Vol. 76, pages 3352 to 3353 (1954), 150 g of 2-methoxy-2,4,6-cycloheptatrien-1-one and 84 g of thiourea were added to 255 g of 28% sodium methoxide/methanol solution and stirred for 30 minutes at room temperature. Further, 600 ml of methanol was added and acetic acid was added until the pH of the resulting solution became 5 or so. The crystals precipitated were separated by filtration and washed with methanol. Next, the thus obtained crystals were added to one liter of methanol and heated under reflux for 30 minutes. After cooling to room temperature, the crystals were separated by filtration and then dried. 125 g of yellow crystals was obtained.

Workup

  1. customThe crystals precipitated
  2. customwere separated by filtration
  3. washwashed with methanol
  4. additionNext, the thus obtained crystals were added to one liter of methanol
  5. temperatureheated
  6. temperatureunder reflux for 30 minutes
  7. temperatureAfter cooling to room temperature
  8. customthe crystals were separated by filtration
  9. customdried

Sources & evidence

ORD record
ord-eb03c6b574f5401bb319c4b39ea4d071
Source dataset
uspto-grants-1991_03
Patent number
US05003077

Reaction notes

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