Potassium Hydroxide → 5-Nitro-6-(2thiazolylthio)-1-indanone ethylene acetal

HRID 1654783노트

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HRID 1654783 반응식
[CH2:1]1[O:17][C:4]2([C:12]3[C:7](=[CH:8][C:9]([N+:14]([O-:16])=[O:15])=[C:10](Br)[CH:11]=3)[CH2:6][CH2:5]2)[O:3][CH2:2]1.[SH:18][C:19]1[S:20][CH:21]=[CH:22][N:23]=1.[OH-].[K+]>N1C=CC=CC=1>[CH2:1]1[O:17][C:4]2([C:12]3[C:7](=[CH:8][C:9]([N+:14]([O-:16])=[O:15])=[C:10]([S:18][C:19]4[S:20][CH:21]=[CH:22][N:23]=4)[CH:11]=3)[CH2:6][CH2:5]2)[O:3][CH2:2]1

참가 물질

5

반응물 3

HCID 14797Potassium HydroxideHCID 10357417HCID 10357417, 화합물HCID 178527881HCID 178527881, 화합물

생성물 1

HCID 108543455-Nitro-6-(2thiazolylthio)-1-indanone ethylene acetal수율 60.8%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
80 °C

실험 절차

The bromide from Step 6 (410 mg, 1.37 mmol) and 2-mercaptothiazole (200 mg, 1.7 mmol) were mixed together in pyridine (3 mL) at room temperature. Aqueous KOH (8M, 213 μL, 1.7 mmol) was added and the resulting mixture was heated with an oil bath at 80° C. for 3 h, then at 100° C. for 1.5 h and finally 75° C. for 16 h. After cooling to room temperature the mixture was diluted and EtOAc and washed with water. The organic layer was dried over MgSO4 and concentrated in vacuo. Purification by flash chromatography on silica gel (from 5% acetone in 2:1 CH2Cl2 -hexanes to 10% acetone in CH2Cl2) yielded 280 mg of the title compound.

후처리

  1. waitfinally 75° C. for 16 h
  2. temperatureAfter cooling to room temperature the mixture
  3. additionwas diluted
  4. washEtOAc and washed with water
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica gel (from 5% acetone in 2:1 CH2Cl2 -hexanes to 10% acetone in CH2Cl2)

출처 및 근거

ORD 기록
ord-e74c525a4e99476790bd579e03d79bc9
출처 데이터셋
uspto-grants-1995_04
특허 번호
US05409944

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