Hydrochloric Acid → HCID 59609613, compound

HRID 1660683Notes

Reaction equation

HRID 1660683 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]1[C:30]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[S:24][C:23]2[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=2.Cl>N1C=CC=CC=1>[C:1]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]1[C:30]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[S:24][C:23]2[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 59609592HCID 59609592, compound

Product 1

HCID 59609613HCID 59609613, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

16.0 g (114 mmol) of benzoyl chloride were added dropwise at 0-5° C. with stirring to a solution of 4.00 g (13.7 mmol) of 10-(2-hydroxyphenyl)phenothiazine in 24 ml of pyridine within 30 min. After stirring at room temperature for 2 h, the reaction solution was heated to 60-65° C. and stirred at this temperature for 15 min. After cooling to room temperature, the suspension was then stirred overnight. After adding 300 ml of ice-water, the suspension was admixed slowly with 19 ml of conc. hydrochloric acid (pH 0.9) and stirred for 1 h. The suspension was filtered through a glass frit. The residue was washed to neutrality with 2 l of water and dried at 60° C. under reduced pressure. 2.87 g (53% of theory) of colorless microcrystals having a melting point of 144-148° C. were obtained.

Workup

  1. temperaturethe reaction solution was heated to 60-65° C.
  2. stirringstirred at this temperature for 15 min
  3. temperatureAfter cooling to room temperature
  4. stirringthe suspension was then stirred overnight
  5. stirringstirred for 1 h
  6. filtrationThe suspension was filtered through a glass frit
  7. washThe residue was washed
  8. customdried at 60° C. under reduced pressure
  9. customwere obtained

Sources & evidence

ORD record
ord-38520b3f6dcc4101ad9f5fcda4cd91a1
Source dataset
uspto-grants-2011_10
Patent number
US08029919B2

Reaction notes

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