Dimethylformamide → 2-Chloro-5-methoxy-1,3-benzoxazole

HRID 13454Notes

Reaction equation

HRID 13454 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.CN(C=O)C.S(Cl)([Cl:20])=O>>[Cl:20][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

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178488270HCID 178488270, compound

Product 1

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

Procedure

The mixture containing 5-methoxybenzoxazole-2-thiol was heated in thionyl chloride with a drop of DMF. The resultant mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was washed with brine and dried and concentrated. Purification on a silica gel column gave 2-chloro-5-methoxybenzoxazole as a white solid. MS: MH+=184.

Workup

  1. concentrationThe resultant mixture was concentrated
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customPurification on a silica gel column

Sources & evidence

ORD record
ord-72ee57f529fb4716b4fa5ff71406d94e
Source dataset
uspto-grants-2010_06
Patent number
US07728010B2

Reaction notes

Loading…