Chloral → HCID 13341953, compound

HRID 2286863Notes

Reaction equation

HRID 2286863 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:12][OH:13].O=[CH:15][C:16]([Cl:19])([Cl:18])[Cl:17]>C(OCC)(=O)C>[Cl:17][C:16]([Cl:19])([Cl:18])[CH:15]1[NH:1][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=2[CH2:12][O:13]1

Participants

4

Reactant 2

HCID 6407ChloralHCID 23460485HCID 23460485, compound

Product 1

HCID 13341953HCID 13341953, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-amino-3-hydroxymethylbenzoate (1 g.) and anhydrous chloral (1 ml.) were mixed together, initially with external ice-cooling, and then on a steam bath for 5 minutes. The product was dissolved in ethyl acetate (100 ml.) and the solution was washed with water (50 ml.), then dried. The solvent was evaporated, and the residue was crystallized from a mixture of ethyl acetate and petroleum ether (b.p. 60°-80 C.) to give methyl 1,2-dihydro-2-trichloromethyl-4H-benzo[d]-[1,3]-oxazine-6-carboxylate, m.p. 178°-179° C.

Workup

  1. temperaturecooling
  2. washthe solution was washed with water (50 ml.)
  3. customdried
  4. customThe solvent was evaporated
  5. customthe residue was crystallized from a mixture of ethyl acetate and petroleum ether (b.p. 60°-80 C.)

Sources & evidence

ORD record
ord-a06e2b787c98477eb528a978393eb531
Source dataset
uspto-grants-1981_05
Patent number
US04268510

Reaction notes

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