Formaldehyde → HCID 22066088, compound

HRID 2101713Notes

Reaction equation

HRID 2101713 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([CH:11]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[Cl:20])[OH:12])=O.C=O.[CH:23]([NH2:25])=O>O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:25]=[CH:23][O:12][C:11]=1[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[Cl:20]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 713FormamideHCID 13602723HCID 13602723, compound

Product 1

HCID 22066088HCID 22066088, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
205 °C

Procedure

A mixture of (+/−)-2,2′,4,4′-tetrachlorobenzoin (1.0 gm, 2.9 mmol) from Step A and paraformaldehyde (0.70 gm, 24 mmol) in formamide (20 mL) was heated to 200-210° C. for 3 hr. The reaction was cooled to rt, diluted with water, and extracted twice with ethyl acetate. The organic layers were washed with brine, dried over sodium sulfate, and evaporated. The residue was purified by flash chromatography, eluting first with 10% ethyl acetate in hexanes to afford 4,5-di-(2,4-dichlorophenyl)oxazole as a higher Rf byproduct and then with 75% ethyl acetate in hexanes to elute the title compound as an oil.

Workup

  1. temperatureThe reaction was cooled to rt
  2. extractionextracted twice with ethyl acetate
  3. washThe organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue was purified by flash chromatography
  7. washeluting first with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c2091b4705df4570a003cce63cdf9a6b
Source dataset
uspto-grants-2009_08
Patent number
US07572785B2

Reaction notes

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