Thionyl Chloride → HCID 3715238, 화합물

HRID 1034336

반응식

HRID 1034336 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 3715238HCID 3715238, 화합물수율 81.6%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-34fb93e35a4e4d21a7f933431d58f302
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05314998

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