Carbon Disulfide → 2-Methyl-9,10-dihydro-benzo[5,6]cyclohepta[1,2-d]oxazol-4-one

HRID 441713Notes

Reaction equation

HRID 441713 reaction equation
[CH3:1][C:2]1[O:3][C:4]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:5]([C:7](Cl)=[O:8])[N:6]=1.C(=S)=S.[Cl-].[Al+3].[Cl-].[Cl-]>C(OCC)(=O)C>[CH3:1][C:2]1[O:3][C:4]2[CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:7](=[O:8])[C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 6451240Aluminum(III) ChlorideHCID 214177332-Methyl-5-(2-phenylethyl)-1,3-oxazole-4-carbonyl chloride

Product 1

HCID 122003742-Methyl-9,10-dihydro-benzo[5,6]cyclohepta[1,2-d]oxazol-4-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.0 g. of 2-methyl-5-phenethyl-4-oxazolecarbonyl chloride (obtainable by Step D, above) in 15 ml. of carbon disulfide, 2.5 g. of anhydrous aluminum chloride added, and the mixture refluxed for 1 hour. The mixture is then cooled, poured on to ice, and extracted twice with 10 ml. portions of chloroform. The extracts are combined, dried over anhydrous sodium sulfate and evaporated (under vacuum) to obtain a solid residue, which is recyrstallized from ethyl acetate to obtain the title compound, m.p. 174°-176°.

Workup

  1. temperaturethe mixture refluxed for 1 hour
  2. temperatureThe mixture is then cooled
  3. additionpoured on to ice
  4. extractionextracted twice with 10 ml
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated (under vacuum)
  7. customto obtain a solid residue, which

Sources & evidence

ORD record
ord-180950944dca4300a9b9ddc596ec1bbd
Source dataset
uspto-grants-1977_08
Patent number
US04042596

Reaction notes

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