Formaldehyde → HCID 19975429, compound

HRID 1440806Notes

Reaction equation

HRID 1440806 reaction equation
[F: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]([Br:22])=[CH:18][CH:17]=1)=[O:14])[C:6]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)([OH:23])[CH2:5]2.C=O.O.[C:34]1(C)C=CC(S(O)(=O)=O)=CC=1>C(#N)C>[F: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]([Br:22])=[CH:20][CH:21]=3)=[O:14])[CH2:34][O:23][C:6]1([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)[CH2:5]2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 521998p-Toluenesulfonic acid monohydrateHCID 54102814HCID 54102814, compound

Product 1

HCID 19975429HCID 19975429, compoundYield 447.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.80 g (0.0017 moles) of the product obtained in Step C, 0.25 g (0.0027 moles) of paraformaldehyde, 50 mg of p-toluene sulfonic acid monohydrate and 45 mL of acetonitrile was refluxed for 30 minutes. The resulting mixture was partitioned between chloroform and saturated aqueous sodium bicarbonate and the aqueous layer was extracted three times with chloroform. The combined organic layers were dried over magnesium sulfate and concentrated to give a yellow solid. The solid was triturated with methanol/water, and dried under vacuum to afford 0.57 g of a yellow solid, m.p. 208°-209° C.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. customThe resulting mixture was partitioned between chloroform and saturated aqueous sodium bicarbonate
  3. extractionthe aqueous layer was extracted three times with chloroform
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give a yellow solid
  7. customThe solid was triturated with methanol/water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-8559115ea1cd4771a4b6593affd1691c
Source dataset
uspto-grants-1996_03
Patent number
US05500438

Reaction notes

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