Formaldehyde → HCID 15790544, compound

HRID 726183Notes

Reaction equation

HRID 726183 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[N:11][NH:12][C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1)=[O:14])[C:6]([C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)([OH:26])[CH2:5]2.C=O.O.[C:37]1(C)C=CC(S(O)(=O)=O)=CC=1>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7]1=[N:11][N:12]([C:13]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:21]=3)=[O:14])[CH2:37][O:26][C:6]1([C:27]1[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=1)[CH2:5]2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 521998p-Toluenesulfonic acid monohydrateHCID 53865386HCID 53865386, compound

Product 1

HCID 15790544HCID 15790544, compoundYield 172.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.30 g (0.0006 moles) of the product obtained in Step D, 0.36 g (0.012 moles) of paraformaldehyde, 50 mg of p-toluene sulfonic acid monohydrate and 30 mL of acetonitrile was refluxed for 1 hour. The resulting mixture was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate and the aqueous layer was extracted twice with CH2Cl2. The combined organic layers were dried over MgSO4 and concentrated to give an oil that was chromatographed on silica gel using 4:1 hexanes-ethyl acetate to give 0.23 g of an oil that solidified on standing, melting point, 213°-214° C.

Workup

  1. temperaturewas refluxed for 1 hour
  2. customThe resulting mixture was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate
  3. extractionthe aqueous layer was extracted twice with CH2Cl2
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. customto give an oil that
  7. customwas chromatographed on silica gel using 4:1 hexanes-ethyl acetate

Sources & evidence

ORD record
ord-c84951224b6244e19e501002a6527050
Source dataset
uspto-grants-1998_01
Patent number
US05708170

Reaction notes

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