Thionyl Chloride → 10-Methylacridan-9-carboxylic acid chloride

HRID 1034584Notes

Reaction equation

HRID 1034584 reaction equation
[CH3:1][N:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]([C:16]([OH:18])=O)[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2.S(Cl)([Cl:21])=O.C1C(N=NC2C=CC(N)=C(S([O-])(=O)=O)C=2)=CC=C(S([O-])(=O)=O)C=1.[Na+].[Na+]>ClCCl>[CH3:1][N:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]([C:16]([Cl:21])=[O:18])[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 75918Benzenesulfonic acid, 2-amino-5-(2-(4-sulfophenyl)diazenyl)-, sodium salt (1:?)HCID 1039934110-Methylacridan-9-carboxylic acid

Product 1

HCID 5452072910-Methylacridan-9-carboxylic acid chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 50 mL round bottom flask equipped with magnetic stirrer and under an argon atmosphere was charged a solution of 0.305 parts of 10-methylacridan-9-carboxylic acid (77) in 15 mL of dichloromethane and cooled to 5° C. (ice-water). Then, 1.05 parts of thionyl chloride was added to the cold yellow acid solution and stirred for 1.5 hr at a temperature below 15° C. The light red brown solution was concentrated under reduced pressure and the residue was dried for 15 min to give acid chloride (78).

Workup

  1. customInto a 50 mL round bottom flask equipped with magnetic stirrer and under an argon atmosphere
  2. concentrationThe light red brown solution was concentrated under reduced pressure
  3. customthe residue was dried for 15 min

Sources & evidence

ORD record
ord-7aa3577afe0645c797e04fc91e72a4c2
Source dataset
uspto-grants-2013_10
Patent number
US08546150B2

Reaction notes

Loading…