Thionyl Chloride → 4-Benzoylamino-naphthalene-1-sulfonyl chloride

HRID 561271

Reaction equation

HRID 561271 reaction equation
[C:1]([NH:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([S:20]([OH:23])(=O)=[O:21])=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:26])=O>CN(C=O)C>[C:1]([NH:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([S:20]([Cl:26])(=[O:23])=[O:21])=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 35301064-Benzoylamino-naphthalene-1-sulfonic acid

Product 1

HCID 161057574-Benzoylamino-naphthalene-1-sulfonyl chlorideYield 88.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the pyridinium salt of 4-benzoylamino-napthalene-1-sulfonic acid (2.4 g, 5.9 mmol) in DMF (10 mL), was added thionyl chloride (0.6 mL, 8.8 mmol). The resultant solution was stirred at 25° C. for 3 hours. The reaction mixture was quenched by pouring into ice water and filtered to give the title compound (1.8 g) a pale white solid. This material was used without further purification. 1H NMR (300 MHz, DMSO) δ 8.88 (d, 1H), 8.09 (d, 2H), 7.97 (d, 2H), 7.55 (m, 6H).

Workup

  1. customThe reaction mixture was quenched
  2. additionby pouring into ice water
  3. filtrationfiltered

Sources & evidence

ORD record
ord-fa665590056b46628fbb304c41c0d49f
Source dataset
uspto-grants-2011_11
Patent number
US08063222B2

Linked notes

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