Benzene, 1-(chloromethyl)-2-fluoro- → HCID 13756053, compound

HRID 1763012Notes

Reaction equation

HRID 1763012 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[C:5]2[C:10]([N:11]=[C:12]3[C:17]=1[C:16](=[O:18])[CH2:15][CH2:14][CH2:13]3)=[CH:9][CH:8]=[CH:7][CH:6]=2.[F:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22]Cl>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[F:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][NH:3][C:4]1[C:5]2[C:10]([N:11]=[C:12]3[C:17]=1[C:16](=[O:18])[CH2:15][CH2:14][CH2:13]3)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

6

Reactant 3

HCID 9580Benzene, 1-(chloromethyl)-2-fluoro-2×HCID 14798Sodium HydroxideHCID 1843619-amino-3,4-dihydroacridin-1(2H)-one

Product 1

HCID 13756053HCID 13756053, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

In a mixture consisting of 150ml of dichloromethane and 100ml of 50% NaOH were comined 5.00 g of 9-amino-3,4-dihydro-acridin-1(2H)-one, 3ml (1 eq) of 2-fluorobenzylchloride and 1.20 g (0.15 eq) of tetrabutylammonium hydrogen sulfate. The bisphasic mixture was mechanically stirred overnight and 3ml of 2-fluorobenzylchloride was again added. After 4 hours of further stirring, the reaction was complete based on thin layer chromatography. The reaction mixture was partitioned between water and dichloromethane and the dichloromethane layer was separated, dried over MgSO4, filtered and evaporated to a solid.

Workup

  1. waitAfter 4 hours of further stirring
  2. customThe reaction mixture was partitioned between water and dichloromethane
  3. customthe dichloromethane layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to a solid

Sources & evidence

ORD record
ord-207f579c2bef4767baf95abd2d84ead2
Source dataset
uspto-grants-1989_05
Patent number
US04835275

Reaction notes

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