Dimethylformamide → 2-Chloro-6-methoxy-1,3-benzoxazole

HRID 512448Notes

Reaction equation

HRID 512448 reaction equation
S[C:2]1[O:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.CN(C=O)C.S(Cl)([Cl:20])=O>>[Cl:20][C:2]1[O:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178488033HCID 178488033, compound

Product 1

HCID 106790422-Chloro-6-methoxy-1,3-benzoxazole

Procedure

Finally, pure 2-mercapto-6-methoxybenzoxazole (4.0 g, 22.2 mmol) was dissolved in thionyl chloride (15 mL). DMF (1 mL) was added to the solution and the reaction mixture was stirred at r.t for 10 min. The solvent was removed under reduced pressure. The crude product was dissolved in ethyl acetate, washed with water, dried over Na2SO4, and concentrated to give crude 2-chloro-6-methoxybenzoxazole, which was purified by chromatography with petroleum ether/ethylacetate (3:1 v/v) to afford 2-chloro-6-methoxybenzoxazole, compound 25, (3.7 g, yield 92%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe crude product was dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give crude 2-chloro-6-methoxybenzoxazole, which
  7. customwas purified by chromatography with petroleum ether/ethylacetate (3:1 v/v)

Sources & evidence

ORD record
ord-2f8313d12f5d43aaba985386929cd55c
Source dataset
uspto-grants-2015_08
Patent number
US09102636B2

Reaction notes

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