Formaldehyde → HCID 19815159, compound

HRID 465975Notes

Reaction equation

HRID 465975 reaction equation
[OH:1][NH:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:18]1(C)C=CC(S(O)(=O)=O)=CC=1.C=O>C1(C)C=CC=CC=1>[OH:1][N:2]1[C:3](=[O:17])[C:4]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:18]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6101p-Toluenesulfonic acidHCID 22271613HCID 22271613, compound

Product 1

HCID 19815159HCID 19815159, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of N-hydroxy-2-(phenylamino)benzamide (1.4 g, 6.15 mmol), p-toluene sulfonic acid (400 ml), and paraformaldehyde (200 mg, 6.75 mmol) in toluene (50 ml) is stirred at room temperature for 30 minutes. The reaction mixture is heated for 10 minutes (in an oil bath preheated to 120°-130° C.) using a Dean-Stark trap to collect water. The reaction mixture is cooled and diluted with ethyl acetate (50 ml) and is extracted with saturated aqueous NaHCO3 (4×50 ml) and water (50 ml). The organic layer is dried (MgSO4) and evaporated. Recrystallization from EtOAc/hexane gives 0.6 g (40%) of 2,3-dihydro-3-hydroxy-1-phenyl-4(1H)-quinazolinone, mp 156°-160° C.

Workup

  1. temperatureThe reaction mixture is heated for 10 minutes (in an oil bath preheated to 120°-130° C.)
  2. customto collect water
  3. temperatureThe reaction mixture is cooled
  4. additiondiluted with ethyl acetate (50 ml)
  5. extractionis extracted with saturated aqueous NaHCO3 (4×50 ml) and water (50 ml)
  6. dry with materialThe organic layer is dried (MgSO4)
  7. customevaporated
  8. customRecrystallization from EtOAc/hexane

Sources & evidence

ORD record
ord-362ccec836864b4b80f801cdf7327867
Source dataset
uspto-grants-1992_10
Patent number
US05155110

Reaction notes

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