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

HRID 1425641Notes

Reaction equation

HRID 1425641 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-ce9ad4eb9c2949558e5d8b0832362b27
Source dataset
uspto-grants-2015_01
Patent number
US08932881B2

Reaction notes

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