Hydrochloric Acid → HCID 66697222, compound

HRID 2386693Notes

Reaction equation

HRID 2386693 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][C:11]([OH:13])=O.C(Cl)(=O)C(Cl)=O.[CH3:20][N:21]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[O:24][CH2:23][C:22]1=[O:31].[Al+3].[Cl-].[Cl-].[Cl-].Cl>O1CCCC1.CN(C)C=O.ClCCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][C:11]([C:28]1[CH:29]=[CH:30][C:25]2[O:24][CH2:23][C:22](=[O:31])[N:21]([CH3:20])[C:26]=2[CH:27]=1)=[O:13]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 890322H-1,4-Benzoxazin-3(4H)-one,4-methyl-HCID 6451240Aluminum(III) ChlorideHCID 153659582-Chloro-5-methoxybenzeneacetic acid

Product 1

HCID 66697222HCID 66697222, compoundYield 92.8%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 111,2-DichloroethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-chloro-5-methoxy-phenyl)-acetic acid (1 g) in tetrahydrofuran (20 ml) were added N,N-dimethylformamide (2 drops) and oxalylchloride (1.03 g). The mixture was stirred overnight at room temperature. The solvent was evaporated; toluene was added and again evaporated. The residue was dried under high vacuum to give the crude acid chloride. To a cooled solution (ice bath) of 4-methyl-2H-1,4-benzoxazin-3(4H)-one (830 mg) in 1,2-dichloroethane (5 ml) was added AlCl3 (1.99 g). The mixture was stirred for 10 min and a solution of the acid chloride in 1,2-dichloroethane (5 ml) was added dropwise. The mixture was stirred at 0° C. for 4.5 h. The mixture was poured into ice water and hydrochloric acid and extracted with dichloromethane. The organic phase was dried (MgSO4), filtered and concentrated. The product was purified by chromatography (SiO2, cyclohexane/EtOAc 1:0=>0:1) to give the title compound (1.6 g) as an off-white solid. MS (m/e)=346.1 [M+H+].

Workup

  1. customThe solvent was evaporated
  2. additiontoluene was added
  3. customagain evaporated
  4. customThe residue was dried under high vacuum
  5. customto give the crude acid chloride
  6. stirringThe mixture was stirred for 10 min
  7. stirringThe mixture was stirred at 0° C. for 4.5 h
  8. extractionextracted with dichloromethane
  9. dry with materialThe organic phase was dried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe product was purified by chromatography (SiO2, cyclohexane/EtOAc 1:0=>0:1)

Sources & evidence

ORD record
ord-8342743b08eb44c9a68b0c0564aadc66
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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