Thionyl Chloride → 2-Chloro-5-methoxy-1,3-benzoxazole

HRID 409298

Reaction equation

HRID 409298 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9](S)=[N:8][C:7]=2[CH:12]=1.S(Cl)([Cl:15])=O>CN(C=O)C.ClCCl>[Cl:15][C:9]1[O:10][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:12][C:7]=2[N:8]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 178488270HCID 178488270, compound

Product 1

HCID 118197122-Chloro-5-methoxy-1,3-benzoxazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
68 °C

Procedure

To a mixture of 5-methoxy-benzooxazole-2-thiol (12.14 g, 0.07 mol) and thionyl chloride were added two drops of DMF. The mixture was stirred at 68° C. for forty minutes and the formation of gas had stopped. The mixture was diluted with dichloromethane, concentrated, and dried in vacuo to give the title compound as a green solid (14.31 g): 1H NMR (CDCl3, 200 MHz): δ=7.36 (m, 1H), 7.13 (m, 1H), 6.92 (m, 1H), 3.84 (s, 3H).

Workup

  1. concentrationconcentrated
  2. customdried in vacuo

Sources & evidence

ORD record
ord-ad94cac211cc4911b474470f072cc2ac
Source dataset
uspto-grants-2014_06
Patent number
US08759373B2

Linked notes

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