Formaldehyde → HCID 53660746, compound

HRID 864655Notes

Reaction equation

HRID 864655 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH2:16][CH:17]([SH:21])[C:18](O)=[O:19])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].[CH2:22]=O.[NH2:24][CH:25]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1(C)C=CC=CC=1>[CH3:4][C:2]([C:5]1[CH:6]=[C:7]([CH2:16][CH:17]2[S:21][CH2:22][N:24]([CH:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:18]2=[O:19])[CH:8]=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:10]=1[OH:11])([CH3:3])[CH3:1]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 7036BenzhydrylamineHCID 11023322HCID 11023322, compound

Product 1

HCID 53660746HCID 53660746, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

3-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-2-mercaptopropanoic acid (2.0 g; 6.45 moles), prepared substantially in accordance with the method described in Example 1A, was suspended in 20 ml of toluene. Under a nitrogen atmosphere, 0.2 g (6.45 mmoles) of paraformaldehyde was added, followed by 1.18 g (6.45 moles) of aminodiphenylmethane. An additional 10 ml of toluene was added and the resulting solution was heated at reflux temperature for 70 minutes with removal of water by means of a Dean-Stark apparatus. The solution was allowed to cool, after which the toluene was distilled off until about 10 ml of a light, brown solution remained. Fifteen milliliters of hexanes were added and the resultant solution was partitioned between ethyl acetate and 1N hydrochloric acid. The organic layer was washed with a saturated sodium bicarbonate solution and a brine solution, dried with sodium sulfate, filtered, and evaporated to provide a foam. The crude product was purified by silica gel chromatography and evaporated under vacuum to provide 2.99 g of a yellow foam. mp 286°-287° C. (dec).

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureat reflux temperature for 70 minutes
  3. customwith removal of water by means of a Dean-Stark apparatus
  4. temperatureto cool
  5. distillationafter which the toluene was distilled off until about 10 ml of a light, brown solution
  6. additionFifteen milliliters of hexanes were added
  7. customthe resultant solution was partitioned between ethyl acetate and 1N hydrochloric acid
  8. washThe organic layer was washed with a saturated sodium bicarbonate solution
  9. dry with materiala brine solution, dried with sodium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. customto provide a foam
  13. customThe crude product was purified by silica gel chromatography
  14. customevaporated under vacuum

Sources & evidence

ORD record
ord-5fd099a5086741b8b8fb262b4de6c512
Source dataset
uspto-grants-1996_10
Patent number
US05563277

Reaction notes

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