Water → HCID 66701480, compound

HRID 2067189Notes

Reaction equation

HRID 2067189 reaction equation
[CH:1]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl[CH2:19][CH:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CS(C)=O.CO>[CH:20]([CH2:19][N:6]1[C:5]2[C:14](=[CH:1][CH:2]=[CH:3][CH:4]=2)[C:13](=[O:15])[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]1=2)=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 962WaterHCID 2015AcridoneHCID 14798Sodium HydroxideHCID 94242Benzene, (3-chloro-1-propenyl)-

Product 1

HCID 66701480HCID 66701480, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

In 84 g of dimethyl sulfoxide (manufactured by Wako Pure Chemical Industries, Ltd.) were dissolved 15 g of 9(10H) acridone (manufactured by Wako Pure Chemical Industries, Ltd.) and 3.4 g of sodium hydroxide (manufactured by Wako Pure Chemical Industries, Ltd.) and the resultant was heated at 45° C. Thereto was dropwise added 17.6 parts by weight of CMS-P (chloromethylstyrene, manufactured by AGC SEIMI CHEMICAL CO., LTD.) and the resultant was further heated and stirred at 50° C. for 5 hours. This reaction liquid was poured into a mixed solution of 30 g of distilled water and 30 g of methanol (manufactured by Wako Pure Chemical Industries, Ltd.) while stirring. The resulting precipitate was separated by filtration and washed with 300 g of a mixed solution of distilled water and methanol at equal weights. The resulting solid was dried under reduced pressure to give 17.5 g of 10-[(styrenyl)methyl]-9-acridanone as a pale yellow solid. Then, 175 g of N-methylpyrrolidone (manufactured by Wako Pure Chemical Industries, Ltd.) was added to the 17.5 g of 10-[(styrenyl)methyl]-9-acridanone and 60.9 g of thioglycerol (manufactured by Sigma Aldrich Co.). This mixture was heated to 65° C. under a nitrogen atmosphere and stirred for 30 minutes, and then 0.14 g of V-65 (2,2′-azobis(2,4-dimethylvaleronitrile) (manufactured by Wako Pure Chemical Industries, Ltd.) was added thereto and stirred for 2 hours. To this reaction solution was added 500 g of a mixed solvent of water and methanol (1:1 in weight ratio). The precipitated crystal was separated by filtration and washed with 100 g of methanol. The resulting solid was dried under reduced pressure to give 22.0 g of Compound M-1 as a pale yellow solid.

Workup

  1. temperaturethe resultant was further heated
  2. customThis reaction liquid
  3. stirringwhile stirring
  4. customThe resulting precipitate was separated by filtration
  5. washwashed with 300 g of a mixed solution of distilled water and methanol at equal weights
  6. customThe resulting solid was dried under reduced pressure

Sources & evidence

ORD record
ord-9163a272a2914d48a111479fe1eacbb4
Source dataset
uspto-grants-2012_10
Patent number
US08293837B2

Reaction notes

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