Formamide → HCID 21290688, compound

HRID 623211Notes

Reaction equation

HRID 623211 reaction equation
S(=O)(=O)(O)O.C([NH2:8])=O.[Cl:9][C:10]1[CH:27]=[CH:26][C:13]([C:14]([O:16][CH:17]([C:23](=O)[CH3:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=O)=[CH:12][CH:11]=1>>[Cl:9][C:10]1[CH:27]=[CH:26][C:13]([C:14]2[O:16][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:23]([CH3:24])[N:8]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 713FormamideHCID 1118Sulfuric AcidHCID 21290692HCID 21290692, compound

Product 1

HCID 21290688HCID 21290688, compoundYield 55.6%

Conditions

Temperature
140 °C

Procedure

19.6 g (0.2 mol) of concentrated sulphuric acid were added dropwise during 10 minutes to 90 g (2 mol) of formamide, the temperature of the solution being held below 10° C. by external cooling, 26.8 g (0.09 mol) of ethyl 2-(4-chlorobenzoyloxy)-3-oxo-butyrate were added and the stirred solution was heated at 140° C. for 2 hours. The cooled suspension was partitioned between 400 ml of water and 300 ml of diethyl ether. The organic phase was washed twice with 200 ml of 1N hydrochloric acid each time and once with 200 ml of water and then filtered to remove suspended solids. The organic phase was dried over magnesium sulphate, filtered and evaporated. The residue was purified by chromatography on silica gel using 20% by volume ethyl acetate in hexane for the elution. After evaporation of the eluate there were obtained 13.3 g (50%) of ethyl 2-(4-chlorophenyl)-4-methyl-5-oxazolecarboxylate of melting point 80°-81° C.

Workup

  1. additionwere added
  2. customThe cooled suspension was partitioned between 400 ml of water and 300 ml of diethyl ether
  3. washThe organic phase was washed twice with 200 ml of 1N hydrochloric acid each time
  4. filtrationonce with 200 ml of water and then filtered
  5. customto remove
  6. dry with materialThe organic phase was dried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by chromatography on silica gel using 20% by volume ethyl acetate in hexane for the elution
  10. customAfter evaporation of the eluate there

Sources & evidence

ORD record
ord-b10f8375ede44eddba4f09e05638a9f0
Source dataset
uspto-grants-1988_09
Patent number
US04774253

Reaction notes

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