Salicylamide → 2,2-dimethyl-3,4-dihydro-2H-1,3-benzoxazin-4-one

HRID 259225

Reaction equation

HRID 259225 reaction equation
C(Cl)(Cl)Cl.[C:5]([NH2:14])(=[O:13])[C:6]1[C:7](=[CH:9][CH:10]=[CH:11][CH:12]=1)[OH:8].O.[C:16]1(C)[C:17](S(O)(=O)=O)=CC=C[CH:21]=1>CC(C)=O>[CH3:21][C:16]1([CH3:17])[NH:14][C:5](=[O:13])[C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[O:8]1

Participants

5

Reactant 3

HCID 5147SalicylamideHCID 6212ChloroformHCID 124969952-Methylbenzenesulfonic acid hydrate

Product 1

HCID 7174282,2-dimethyl-3,4-dihydro-2H-1,3-benzoxazin-4-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A 500-ml flask was charged with 250 ml of chloroform, 27.4 g (0.2 mol) of salicylamide, 23.2 g (0.4 mol) of acetone and 2.7 g of toluene sulfonic acid monohydrate. The flask was equipped with a Soxhlet extraction vessel containing 36.7 g of molecular sieves (Linde Type 3A, 1/16 inch) in the thimble. The reaction mixture was refluxed for 24 hours. Then fresh sieves were placed in the Soxhlet and 10 g of acetone was added to the reaction mixture. Reflux was continued for 24 hours.

Workup

  1. customThe flask was equipped with a Soxhlet extraction vessel
  2. temperatureThe reaction mixture was refluxed for 24 hours
  3. additionwas added to the reaction mixture
  4. temperatureReflux

Sources & evidence

ORD record
ord-b2ffb7e073fb4b8f88697099e8fecc7d
Source dataset
uspto-grants-1977_07
Patent number
US04036960

Linked notes

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