Methane → AC1LJDFP

HRID 1764205Notes

Reaction equation

HRID 1764205 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([NH:8][NH2:9])=[O:7])[N:3]=[CH:2]1.[CH:10](OCC)(OCC)OCC.C1(OC2C=CC=CC=2)C=CC=CC=1.C>CO.C(O)C>[C:6]1(=[O:7])[NH:8][N:9]=[CH:10][N:3]2[CH:2]=[N:1][CH:5]=[C:4]12

Participants

7

Reactant 4

HCID 297MethaneHCID 7583Diphenyl EtherHCID 31214Ethyl orthoformateHCID 178514423HCID 178514423, compound

Product 1

HCID 948878AC1LJDFP

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
240 °C

Procedure

A mixture of 6.30 gm. of imidazole-4-carboxylic acid hydrazide [Jones et al., J.A.C.S. 71, 2444 (1949)], 63 ml. of triethyl orthoformate and 500 ml. of ethanol is stirred and refluxed for 81/2 hours. The mixture is concentrated in vacuo to a solid. A 100 ml. portion of diphenyl ether is added and the mixture is heated at 240° C. for 15 minutes. The mixture is cooled to room temperature, petroleum ether is added and a solid is collected. This solid is boiled with 150 ml. of methanol. The insoluble portion is collected by filtration and saved. The filtrate is evaporated to give a solid which is heated with 100 ml. of diphenyl ether at reflux for 15 minutes. Cooling to room temperature and the addition of petroleum ether produces a solid. This solid is combined with the above solid, boiled with 600 ml. of methanol and treated with charcoal. The mixture is filtered. The filtrate is boiled down to 35 ml. and cooled giving a solid. This solid is boiled with 50 ml. of ethanol and the hot mixture is filtered. The solid is boiled with 200 ml. of methanol and the insoluble solid is collected by filtration and saved. The filtrate is boiled down to 75 ml. and cooled giving a second solid. These two solids are combined giving the desire product, m.p. 294°-305° C.

Workup

  1. additionA mixture of 6.30 gm
  2. temperaturerefluxed for 81/2 hours
  3. concentrationThe mixture is concentrated in vacuo to a solid
  4. additionportion of diphenyl ether is added
  5. temperatureThe mixture is cooled to room temperature
  6. additionpetroleum ether is added
  7. customa solid is collected
  8. filtrationThe insoluble portion is collected by filtration
  9. customThe filtrate is evaporated
  10. customto give a solid which
  11. temperatureis heated with 100 ml
  12. temperatureCooling to room temperature
  13. customproduces a solid
  14. filtrationThe mixture is filtered
  15. temperatureand cooled
  16. customgiving a solid
  17. filtrationof ethanol and the hot mixture is filtered
  18. filtrationof methanol and the insoluble solid is collected by filtration
  19. temperatureand cooled
  20. customgiving a second solid
  21. customThese two solids are combined giving the desire product, m.p. 294°-305° C.

Sources & evidence

ORD record
ord-a396d553f97c4274a114ed6e7e8af1d8
Source dataset
uspto-grants-1978_09
Patent number
US04115572

Reaction notes

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