Thionyl Chloride → HCID 3715238, compound

HRID 1034336

Reaction equation

HRID 1034336 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([S:21]([O-:24])(=[O:23])=O)[C:5]2[C:10]([C:11]=1[NH:12][C:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[NH+:25]1[CH:30]=[CH:29]C=[CH:27][CH:26]=1.S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH2:26]([N:25]([CH2:30][CH3:29])[S:21]([C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:11]2[N:12]=[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:1][C:2]=2[CH:3]=1)(=[O:24])=[O:23])[CH3:27]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19378056pyridinium 3-hydroxy-4-(N-benzoylamino)-1-naphthalenesulfonate

Product 1

HCID 3715238HCID 3715238, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3.43 g pyridinium 3-hydroxy-4-(N-benzoylamino)-1-naphthalenesulfonate and 10 ml thionyl chloride was refluxed for 3.5 hours. Toluene (20 ml) was added and the excess thionyl chloride was distilled off with toluene under reduced pressure. The solid residue was dissolved in 50 ml methylene chloride and 10 ml diethylamine was added portionwise while stirring. After 30 min, the reaction mixture was poured into 100 ml ice-water and extracted with 100 ml dichloromethane. The organic phase was separated, washed with water, and dried over sodium sulfate. Evaporation of the solvent gave 2.52 g N,N-diethyl-2-phenylnaphth[1,2-d]oxazole-5-sulfonamide of high purity by NMR. Recrystallization from 95% ethanol gave an analytical sample, m.p. 157° C.

Workup

  1. temperaturewas refluxed for 3.5 hours
  2. distillationthe excess thionyl chloride was distilled off with toluene under reduced pressure
  3. dissolutionThe solid residue was dissolved in 50 ml methylene chloride
  4. addition10 ml diethylamine was added portionwise
  5. additionthe reaction mixture was poured into 100 ml ice-water
  6. extractionextracted with 100 ml dichloromethane
  7. customThe organic phase was separated
  8. washwashed with water
  9. dry with materialdried over sodium sulfate
  10. customEvaporation of the solvent

Sources & evidence

ORD record
ord-34fb93e35a4e4d21a7f933431d58f302
Source dataset
uspto-grants-1994_05
Patent number
US05314998

Linked notes

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