Methane → HCID 136398797, compound

HRID 26640Notes

Reaction equation

HRID 26640 reaction equation
Cl.N[OH:3].[C:4]1([C:10]2[O:14][C:13]([CH:15]=[N:16]N3CC(=O)NC3=O)=[N:12][CH:11]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.C>C(O)(=O)C>[C:4]1([C:10]2[O:14][C:13]([CH:15]=[N:16][OH:3])=[N:12][CH:11]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 962WaterHCID 443297Hydroxyamine hydrochloride2×HCID 58002885HCID 58002885, compound

Product 1

HCID 136398797HCID 136398797, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Hydroxylamine hydrochloride (54 g, 0.78 mole) and 1-[[[5-phenyl-2-oxazolyl]methylene]amino]-2,4-imidazolidinedione (105 g, 0.39 mole) were refluxed with stirring in a solution of water (100 ml) and glacial acetic acid (1.0 l.) for five hrs. An additional 54 g of hydroxylamine hydrochloride was added while the mixture was refluxed another five hrs. The hot solution was treated with Darco, filtered and poured into water (5.0 l.). The solid was again refluxed in a mixture of hydroxylamine hydrochloride (50 g), acetic anhydride (800 ml) and water (80 ml) for four hrs. The solution was cooled, poured into water (3.0 l.) and the resulting solid was collected and dried (48 g, 65%). Recrystallization of a sample from acetonitrile gave product of analytical purity, m.p. 208°-210°.

Workup

  1. temperaturewas refluxed another five hrs
  2. filtrationfiltered
  3. additionpoured into water (5.0 l.)
  4. temperatureThe solid was again refluxed in a mixture of hydroxylamine hydrochloride (50 g), acetic anhydride (800 ml) and water (80 ml) for four hrs
  5. temperatureThe solution was cooled
  6. additionpoured into water (3.0 l.)
  7. customthe resulting solid was collected
  8. customdried (48 g, 65%)
  9. customRecrystallization of a sample from acetonitrile
  10. customgave product of analytical purity, m.p. 208°-210°

Sources & evidence

ORD record
ord-f6f21de6e4424f9db50e18fefc2c2d19
Source dataset
uspto-grants-1979_04
Patent number
US04151168

Reaction notes

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