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

HRID 1654783Notes

Reaction equation

HRID 1654783 reaction equation
[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

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 10357417HCID 10357417, compoundHCID 178527881HCID 178527881, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-e74c525a4e99476790bd579e03d79bc9
Source dataset
uspto-grants-1995_04
Patent number
US05409944

Reaction notes

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