Water → Dibenzo[b,e][1,4]oxazepin-11(5H)-one

HRID 1692645Notes

Reaction equation

HRID 1692645 reaction equation
O[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH:14]1[C:10]2[C:11](=[O:13])[O:12][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[NH:8][C:9]=2[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 4385882-(2-Hydroxy-phenylamino)-benzoic acid

Product 1

HCID 12701785Dibenzo[b,e][1,4]oxazepin-11(5H)-oneYield 53%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-(2-Hydroxy-phenylamino)-benzoic acid (2.0 g, 9 mmol) and p-toluenesulfonic acid (0.5 g) in toluene (200 ml) was heated under N2 with the H2O formed being collected in a Dean-Stark receiver. Upon completion, the organic layer was washed with saturated NaHCO3, dried over anhydrous MgSO4, filtered, and evaporated by a rotatory evaporator to obtain the product (1.0 g, 53%).

Workup

  1. customformed
  2. custombeing collected in a Dean-Stark receiver
  3. washUpon completion, the organic layer was washed with saturated NaHCO3
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated by a rotatory evaporator

Sources & evidence

ORD record
ord-2a68cc3119274eed8dd17765321daa3c
Source dataset
uspto-grants-2012_04
Patent number
US08158623B2

Reaction notes

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