Acetic Acid → HCID 10657978, compound

HRID 220609Notes

Reaction equation

HRID 220609 reaction equation
[Cl:1][C:2]1[CH:3]=C[CH:5]=[C:6]2NC(=O)OC(=O)[C:7]=12.[C:14]1([NH2:21])[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH2:20].O.[C:23]([OH:26])(=O)[CH3:24]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:20][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[NH:21][C:23](=[O:26])[C:24]=2[CH:3]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 7243O-PhenylenediamineHCID 6390585-chloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 10657978HCID 10657978, compound

Conditions

Temperature
100 °C

Procedure

6-Chloro isatoic anhydride (0.1 mol) and 1,2-phenylenediamine (0.1 mol) were dissolved in acetic acid (90%) and the mixture heated at 100° C. for 2.5 hrs. The mixture was poured into water and extracted with ethyl acetate, neutralized, dried and 2-chloro-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-11-one was isolated (94%) after removal of solvent under reduced pressure.

Workup

  1. extractionextracted with ethyl acetate
  2. customdried

Sources & evidence

ORD record
ord-3711c68810ac4cc4a9ff768a19786eec
Source dataset
uspto-grants-2012_06
Patent number
US08202989B2

Reaction notes

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