Dimethylformamide → Methyl 2-chloro-1,3-benzoxazole-6-carboxylate

HRID 409995Notes

Reaction equation

HRID 409995 reaction equation
S[C:2]1[O:3][C:4]2[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.O=S(Cl)[Cl:17].CN(C=O)C>>[Cl:17][C:2]1[O:3][C:4]2[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178497334HCID 178497334, compound

Product 1

HCID 58433755Methyl 2-chloro-1,3-benzoxazole-6-carboxylate

Procedure

To Compound 4 (2 g, 9.5 mmol), SOCl2 (9.8 ml, 134 mmol) and DMF (0.8 mL, 10 mmol) was added at room temperature. The reaction mixture heated to reflux for 15 min. The solvent was removed under reduced pressure. The crude oil was azeotroped with xylene twice.

Workup

  1. temperatureThe reaction mixture heated
  2. temperatureto reflux for 15 min
  3. customThe solvent was removed under reduced pressure
  4. customThe crude oil was azeotroped with xylene twice

Sources & evidence

ORD record
ord-c894aa49e5ff4011a3709e8e3952a4d1
Source dataset
uspto-grants-2014_06
Patent number
US08759539B2

Reaction notes

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