Phenyl isocyanate → N-[2-(4-Oxo-4H-3,1-benzoxazin-2-yl)phenyl]-N'-phenylurea

HRID 458479Notes

Reaction equation

HRID 458479 reaction equation
[CH:1]1[CH:6]=[C:5]([C:7]([NH:9][C:10]2[C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=[CH:12][CH:11]=2)=O)[C:4]([NH2:19])=[CH:3][CH:2]=1.[C:20]1([N:26]=[C:27]=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CC(OC(C)=O)=O>CC(CC)=O>[C:20]1([NH:26][C:27]([NH:19][C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][C:5]=2[C:7]2[O:18][C:16](=[O:17])[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=2)=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 7918Acetic AnhydrideHCID 691582-((2-Aminobenzoyl)amino)benzoic acid

Product 1

HCID 18442119N-[2-(4-Oxo-4H-3,1-benzoxazin-2-yl)phenyl]-N'-phenylurea

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

A 250 ml three-neck bottle was charged under room temperature with 12.8 g [0.05 mol] anthranoylanthranilic acid and 100 ml methylethylketone. Under stirring 5.95 g [0.05 mol] phenylisocyanate was added and heated for about 4 hours under reflux about 80° C.). After this the suspension was cooled down to about. 40° C. Then 40 ml acetanhydrid was added and then heated additionally for 3 hours. After cooling down to 10° C. the precipitate was sucked off, washed with acetone and dried at 50° C. under normal pressure.

Workup

  1. additionwas added
  2. temperatureheated for about 4 hours
  3. temperatureAfter this the suspension was cooled down to about
  4. custom40° C
  5. temperatureheated additionally for 3 hours
  6. temperatureAfter cooling down to 10° C. the precipitate
  7. washwashed with acetone
  8. customdried at 50° C. under normal pressure

Sources & evidence

ORD record
ord-3dd35886ae89473590f1bf021c919385
Source dataset
uspto-grants-2007_03
Patent number
US07192471B2

Reaction notes

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