9,10-Phenanthrenedione → 10-[(Benzothiazol-2-yl)azo]phenanthren-9-ol

HRID 1266932Notes

Reaction equation

HRID 1266932 reaction equation
[CH:1]1[C:14]2[C:13](=O)[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH:17]([C:19]1[S:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1)[NH2:18]>C(O)(=O)C>[S:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=[C:19]1[N:17]=[N:18][C:13]1[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12]=1[OH:16]

Participants

4

Reactant 2

HCID 67639,10-Phenanthrenedione2×HCID 119882-Benzothiazolinone, hydrazone

Product 1

HCID 13571851910-[(Benzothiazol-2-yl)azo]phenanthren-9-ol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
105 °C

Procedure

A reaction flask was loaded with acetic acid (50 ml) and 9,10-phenanthrenequinone (4.2 g), and the temperature was raised to 105° C. with stirring to dissolve 9,10-phenanthrenequinone. To this mixture, 2-hydrazinobenzothiazole (3.3 g) was added in three hours. After stirring at 100 to 110° C. for one hour, the reaction mixture was filtrated. The filtrated crystals were washed with methanol and dried to give intended crystals (3.9 g).

Workup

  1. stirringAfter stirring at 100 to 110° C. for one hour
  2. filtrationthe reaction mixture was filtrated
  3. washThe filtrated crystals were washed with methanol
  4. customdried
  5. customto give

Sources & evidence

ORD record
ord-ad8ea9069aed447fb8fa2dd687c237c9
Source dataset
uspto-grants-2003_04
Patent number
US06551682B1

Reaction notes

Loading…