O-Phenylenediamine → HCID 178517136, compound

HRID 1429085Notes

Reaction equation

HRID 1429085 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10](=O)[C:11]([O:13]CC)=O.[C:17]1([NH2:24])[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH2:23]>CCO>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([OH:13])=[N:23][C:18]2[C:17]([N:24]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 66521765Ethyl (1,3-benzothiazol-2-yl)(oxo)acetate

Product 1

HCID 178517136HCID 178517136, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 2-(benzo[d]thiazol-2-yl)-2-oxoacetate (Example 13a, 655 mg, 2.78 mmol) in EtOH (5.6 mL) was added o-phenylenediamine (300 mg, 2.78 mmol). The reaction mixture was heated with stiffing at 90° C. for 1 hr (a yellow/green solid appeared quickly), cooled to 0° C., and the solid filtered and rinsed with cold EtOH. The solid was dried under vacuum overnight to provide the title compound (3-(benzo[d]thiazol-2-yl)quinoxalin-2-ol, 313 mg, 40% yield) as a yellow green solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. filtrationthe solid filtered
  3. washrinsed with cold EtOH
  4. customThe solid was dried under vacuum overnight

Sources & evidence

ORD record
ord-52c1814172fc4b88bb2dd7b8d7b9e20d
Source dataset
uspto-grants-2015_01
Patent number
US08937041B2

Reaction notes

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