Oxalyl chloride → HCID 18989143, compound

HRID 2395564Notes

Reaction equation

HRID 2395564 reaction equation
[C:1](Cl)(=O)C(Cl)=O.[C:7]([C:11]1[O:12][C:13]2[C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=[C:16]([Cl:23])[C:14]=2[N:15]=1)([CH3:10])([CH3:9])[CH3:8]>CN(C)C=O>[C:7]([C:11]1[O:12][C:13]2[C:19]([C:20]([O:22][CH3:1])=[O:21])=[CH:18][CH:17]=[C:16]([Cl:23])[C:14]=2[N:15]=1)([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 18916423HCID 18916423, compound

Product 1

HCID 18989143HCID 18989143, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

Oxalyl chloride (2.6 ml) was added dropwise to a stirred suspension of 2-t-butyl-4-chloro-1,3-benzoxazole-7-carboxylic acid (6.2 g). Dry N,N-dimethylformamide (3 drops) was added and the mixture stirred at reflux for 2 hours and evaporated. Dichloromethane was added and the solution added dropwise to a stirred solution of methanol (dry, 3.0 ml) and triethylamine (dry, 10 ml) in dichloromethane at 0° C. After stirring at ambient temperature for 18 hours, the mixture was washed with hydrochloric acid (2M) water, sodium carbonate (2M), water, then dried magnesium sulphate) and evaporated to give methyl 2-t-butyl-4-chloro-1,3-benzoxazole-7-carboxylate (5.7 g) as a light brown solid, m.p. 130°-131° C.

Workup

  1. temperatureat reflux for 2 hours
  2. customevaporated
  3. additionDichloromethane was added
  4. additionthe solution added dropwise to a stirred solution of methanol (dry, 3.0 ml) and triethylamine (dry, 10 ml) in dichloromethane at 0° C
  5. stirringAfter stirring at ambient temperature for 18 hours
  6. washthe mixture was washed with hydrochloric acid (2M) water, sodium carbonate (2M), water
  7. customdried magnesium sulphate) and evaporated

Sources & evidence

ORD record
ord-56dbbb17dd8b45cb9c9f40feee47778e
Source dataset
uspto-grants-1996_02
Patent number
US05489570

Reaction notes

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