Water → HCID 57493916, 화합물

HRID 508351

반응식

HRID 508351 반응식
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([NH2:9])[S:8][C:4]=2[CH:3]=1.[CH3:12][C:13](=O)[CH2:14][CH2:15][C:16](=O)[CH3:17].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.O>C1C=CC=CC=1>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([N:9]3[C:16]([CH3:17])=[CH:15][CH:14]=[C:13]3[CH3:12])[S:8][C:4]=2[CH:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 80352,5-HexanedioneHCID 851492-Benzothiazolamine, 6-bromo-HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

생성물 1

HCID 57493916HCID 57493916, 화합물수율 84%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

A solution 6-bromobenzo[d]thiazol-2-amine (5.75 g, 25.1 mmol), hexane-2,5-dione (2.95 mL, 25.1 mmol), and PPTS (0.95 g, 3.76 mmol) in benzene (100 ml) was refluxed for 16 h while water was removed with a Dean-Stark trap. The cooled mixture was poured into EtOAc (100 mL) and extracted with saturated aq. NaHCO3 (2×100 mL) and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using 9:1 EtOAc:hexanes as the eluent to give the title compound as an orange oil (6.46 g, 84%).

후처리

  1. customwas removed with a Dean-Stark trap
  2. additionThe cooled mixture was poured into EtOAc (100 mL)
  3. extractionextracted with saturated aq. NaHCO3 (2×100 mL) and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography on silica gel using 9:1 EtOAc

출처 및 근거

ORD 기록
ord-820f38f64ed24e64920365a25f92ae34
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09095590B2

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