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

HRID 580704Notes

Reaction equation

HRID 580704 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, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

In a mixture consisting of 150 ml of dichloromethane and 100 ml of 50% NaOH were combined 5.00 g of 9-amino-3,4-dihydroacridin-1(2H)-one, 3 ml (1 eq) of 2-fluorobenzylchloride and 1.20 g (0.15 eg) of tetrabutylammonium hydrogen sulfate. The biphasic mixture was mechanically stirred overnight and 3 ml 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. The solid was purified by chromatography on silica gel (EtOAc) and the resultant product was recrystallized from 1:4 EtOAc/toluene to yield 4.09 g (54%) of a solid, melting point 163.5°-164° C.

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
  7. customThe solid was purified by chromatography on silica gel (EtOAc)
  8. customthe resultant product was recrystallized from 1:4 EtOAc/toluene

Sources & evidence

ORD record
ord-e5629edf0ed44d5ab4bffd05dc0c8869
Source dataset
uspto-grants-1988_06
Patent number
US04754050

Reaction notes

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