Oxalyl chloride → 3-Methyl-2-oxo-1,3-benzoxazole-5-carbonyl chloride

HRID 2096830Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2096830
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9](C(O)=O)=[CH:10][C:5]=2[O:4][C:3]1=[O:14].C(Cl)(=O)[C:16]([Cl:18])=[O:17]>C(Cl)Cl.CN(C=O)C>[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([C:16]([Cl:18])=[O:17])[CH:9]=[CH:10][C:5]=2[O:4][C:3]1=[O:14]

Komponenten

5

Edukt 2

HCID 65578Oxalyl chlorideHCID 151228833-Methyl-2-oxo-1,3-benzoxazole-6-carboxylic acid

Produkt 1

HCID 104431423-Methyl-2-oxo-1,3-benzoxazole-5-carbonyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 3-methyl-2-oxo-2,3-dihydro-benzooxazole-6-carboxylic acid (1.0 g, [CAS Reg. No. 140934-94-7]) in CH2Cl2 (14 mL) were added two drops of DMF and oxalylchloride (0.71 mL). The mixture was stirred at room temperature for 1 hour and was then concentrated to dryness. 1,2-Dimethoxyethane (20 mL) was added and the solvent was evaporated again to give the crude acid chloride (3-methyl-2-oxo-2,3-dihydro-benzooxazole-6-carbonyl chloride). To a suspension of zinc powder (677 mg) in 1,2-dimethoxyethane (8 mL) was added tetrakis(triphenylphosphine)palladium(0) (60 mg). A suspension of the acid chloride in 1,2-dimethoxyethane (8 mL) was added. The mixture was cooled in an ice bath and a solution of 4-bromo-1-bromomethyl-2-chloro-benzene (1.47 g, [CAS Reg. No. 89720-77-4]) in 1,2-dimethoxyethane (10 mL) was slowly added over a period of 15 minutes. The mixture was stirred for 10 minutes at 0° C. and then for 2 hours at r.t. The reaction mixture was poured into ice and basified with sat. NaHCO3. The aqueous phase was then extracted two times with ethyl acetate and the organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. Ethyl acetate (20 mL) was added to the resulting precipitate and the suspension was stirred for 1 hour at r.t. The solid was filtered off and dried in vacuo. The title compound was obtained as an off-white solid (747 mg, 38%). MS (neg. ion, m/e)=380.2 [(M−H)−].

Aufarbeitung

  1. concentrationwas then concentrated to dryness
  2. addition1,2-Dimethoxyethane (20 mL) was added
  3. customthe solvent was evaporated again

Quellen und Nachweise

ORD-Eintrag
ord-fc43c50bdc0c43c8b923c9dcf2888796
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450313B2

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