Water → HCID 20134101, compound

HRID 580503Notes

Reaction equation

HRID 580503 reaction equation
[NH2:1][C:2]1[C:11]2[C:10](=[O:12])[CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=[C:4]2[S:13][CH:14]=[CH:15][C:3]=12.[OH-].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CS(C)=O>[CH2:18]([NH:1][C:2]1[C:11]2[C:10](=[O:12])[CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=[C:4]2[S:13][CH:14]=[CH:15][C:3]=12)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl Bromide2×HCID 14797Potassium Hydroxide2×HCID 142293784-Amino-7,8-dihydrothieno[2,3-b]quinolin-5(6H)-one

Product 1

HCID 20134101HCID 20134101, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Amino-7,8-dihydrothieno[2,3-b]quinolin-5(6H)-one (6.21 g) was dissolved in 60 ml of dimethylsulfoxide (DMSO). Potassium hydroxide (2.3 g, calculated as 85%), which had been pulverized under pentane, was added to the reaction mixture. After 30 minutes 5.0 g of benzyl bromide was added, and after an additional 30 minutes, 1.0 g of potassium hydroxide and 2.0 g of benzyl bromide were added. After a total reaction time of 90 minutes, 200 ml of water was added to the reaction mixture, causing a gummy precipitate to separate. The crude product was collected by filtration and purified by flash chromatography (10% ethyl acetate/dichloromethane) followed by recrystallization from ethyl acetate. Obtained in this manner was 2.35 g of analytically pure product, mp 159°-160°.

Workup

  1. additionwas added to the reaction mixture
  2. customto separate
  3. filtrationThe crude product was collected by filtration
  4. custompurified by flash chromatography (10% ethyl acetate/dichloromethane)
  5. customfollowed by recrystallization from ethyl acetate
  6. customObtained in this manner

Sources & evidence

ORD record
ord-bf2a0981c7bd4a5c9b2797a1e9f0f760
Source dataset
uspto-grants-1988_06
Patent number
US04753950

Reaction notes

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