Phenyl isocyanate → HCID 10753928, compound

HRID 1855921Notes

Reaction equation

HRID 1855921 reaction equation
[NH:1]1[CH:5]([C:6]([O:8][CH3:9])=[O:7])[CH2:4][CH2:3][C:2]1=[O:10].C(N(CC)CC)C.[C:18]1([N:24]=[C:25]=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(OCC)(=O)C>[C:18]1([NH:24][C:25]([N:1]2[CH:5]([C:6]([O:8][CH3:9])=[O:7])[CH2:4][CH2:3][C:2]2=[O:10])=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 500249Methyl 5-oxo-DL-prolinate

Product 1

HCID 10753928HCID 10753928, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In this example, 14.3 g of methyl 2-pyrolidone-5-carboxylate and 10.1 g triethylamine are dissolved in 100 ml of ethyl acetate. Phenyl isocyanate (11.9 g) is added thereto, and the resulting solution is left standing at room temperature overnight. The reaction mixture is then filtered, and the filtrate is washed twice with 100 ml of 1N hydrochloric acid, and then three times with 100 ml water. Then, the filtrate is dried over anhydrous sodium sulfate, and then filtered. The filtrate is concentrated under reduced pressure, and the resulting viscous material is dissolved in 100 ml ether, admixed with 100 ml n-hexane, and recrystallized, whereby methyl 1-phenylcarbamoyl-2-pyrolidone-5-carboxylate (compound number 4; 17.5 g; mp 91°-92° C.) is obtained. Yield: 66.8%.

Workup

  1. waitthe resulting solution is left
  2. filtrationThe reaction mixture is then filtered
  3. washthe filtrate is washed twice with 100 ml of 1N hydrochloric acid
  4. dry with materialThen, the filtrate is dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated under reduced pressure
  7. dissolutionthe resulting viscous material is dissolved in 100 ml ether
  8. customrecrystallized

Sources & evidence

ORD record
ord-8afcddf3095a405793f3c912d59feb68
Source dataset
uspto-grants-1980_08
Patent number
US04217130

Reaction notes

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