Toluene → HCID 19966771, compound

HRID 976226Notes

Reaction equation

HRID 976226 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.C([N:13]([CH2:16][CH3:17])CC)C.C([O:21]C(C)C)(C)C.[C:25]1([CH3:31])C=CC=C[CH:26]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16](=[NH:13])[C:17](=[C:25]([CH3:31])[CH3:26])[O:10][C:9]2=[O:21])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 76934-Chlorophenyl IsocyanateHCID 7914Diisopropyl EtherHCID 8471Triethylamine

Product 1

HCID 19966771HCID 19966771, compound

Procedure

A round-bottomed flask (200 cc) equipped with a dropping funnel was charged with 4-chlorophenyl isocyanate (11.3 g, 73.7 mmol) and triethylamine (0.5 mL), as well as isopropyl ether (40 mL) and toluene (30 mL) and methacrolein cyanohydrin (8.94 g, 92.1 mmol) was dropwise added slowly with stirring at room temperature. After the addition, the mixture was stirred at room temperature for an additional 12 h. After completion of the reaction, the precipitating solids was recovered by filtration, washed with ether (5 mL×2) and hexane (5 mL×2) and subsequently dried to give 3-(4-chlorophenyl)-4-imino-5-isopropylideneoxazolidine-2-one (compound 3) as a white crystal (7.40 g; yield, 40.1%).

Workup

  1. customA round-bottomed flask (200 cc) equipped with a dropping funnel
  2. additionAfter the addition
  3. stirringthe mixture was stirred at room temperature for an additional 12 h
  4. customAfter completion of the reaction
  5. filtrationthe precipitating solids was recovered by filtration
  6. washwashed with ether (5 mL×2) and hexane (5 mL×2)
  7. customsubsequently dried
  8. customto give

Sources & evidence

ORD record
ord-091c3af3f86d4496af813cf19fef8afa
Source dataset
uspto-grants-1997_03
Patent number
US05612289

Reaction notes

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