1,2-Dimethoxyethane → N-(3',4'-Dichlorophenyl)-3,4-dimethyl-2-methyl-carbamoyloxy-5-oxo-2,5-dihydropyrrole

HRID 27189Notes

Reaction equation

HRID 27189 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12]([CH3:15])=[C:11]([CH3:16])[CH:10]2[OH:17])[CH:5]=[CH:6][C:7]=1[Cl:8].C[N:19]=[C:20]=[O:21].[CH3:22]OCCOC>C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:10](=[O:17])[C:11]([CH3:16])=[C:12]([CH3:15])[C:13]2([O:14][C:20](=[O:21])[NH2:19])[CH3:22])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 12228Methyl IsocyanateHCID 13069714N-(3',4'-Dichlorophenyl)-3,4-dimethyl-2-hydroxy-5-oxo-2,5-dihydropyrrole

Product 1

HCID 86736277N-(3',4'-Dichlorophenyl)-3,4-dimethyl-2-methyl-carbamoyloxy-5-oxo-2,5-dihydropyrrole

Reagents, catalysts & solvents 1

HCID 8471TriethylamineCatalyst

Procedure

16.3 g of N-(3',4'-dichlorophenyl)-3,4-dimethyl-2-hydroxy-5-oxo-2,5-dihydropyrrole (see Example 3) is put together with 2 drops of triethylamine in 10 ml of glyme (ethylene glycol dimethyl ether), and 3.8 g of methylisocyanate is then added. After 24 hours, the reaction solution is filtered with a filtering auxiliary (Hyflo®) and the filtrate is concentrated by evaporation to leave an oil, which is crystallised in methanol. In this manner is obtained 15 g (76% of theory) of the above product in the form of yellowish crystals, m.p. 141°-142°.

Workup

  1. additionis then added
  2. filtrationthe reaction solution is filtered with a filtering auxiliary (Hyflo®)
  3. concentrationthe filtrate is concentrated by evaporation
  4. customto leave an oil, which
  5. customis crystallised in methanol
  6. customIn this manner is obtained 15 g (76% of theory) of the above product in the form of yellowish crystals, m.p. 141°-142°

Sources & evidence

ORD record
ord-c00bccc821804a499ee7aafb396bbbca
Source dataset
uspto-grants-1980_09
Patent number
US04220655

Reaction notes

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