Methanesulfonic Acid → 7-n-butyloxymethyl-(1H,3H,5H)-(1)-benzopyrano-(2,3-d)-pyrimidine-4-one-2-thione

HRID 848742

Reaction equation

HRID 848742 reaction equation
[OH:1][CH2:2][C:3]1[CH:10]=[C:7]([CH:8]=O)[C:6]([OH:11])=[CH:5][CH:4]=1.[NH:12]1[C:19](=O)[CH2:18][C:16](=[O:17])[NH:15][C:13]1=[S:14].CS(O)(=O)=O>C(O)CCC>[CH2:2]([O:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:19]3[NH:12][C:13](=[S:14])[NH:15][C:16](=[O:17])[C:18]=3[CH2:8][C:7]=2[CH:10]=1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 531422-Hydroxy-5-(hydroxymethyl)benzaldehydeHCID 2723628Thiobarbituric acid

Product 1

HCID 205642577-n-butyloxymethyl-(1H,3H,5H)-(1)-benzopyrano-(2,3-d)-pyrimidine-4-one-2-thione

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a solution of 5-hydroxymethyl-salicylaldehyde (5.8 g.) and 2-thiobarbituric acid (6 g.) in n-butanol (100 ml.) add methanesulfonic acid (10 ml.) and heat to reflux, with stirring, for 1 hour. Cool, filter and wash the solid with ethanol and ether to yield 7-n-butyloxymethyl-(1H,3H,5H)-(1)-benzopyrano-(2,3-d)-pyrimidine-4-one-2-thione.

Workup

  1. temperatureheat
  2. temperatureto reflux
  3. temperatureCool
  4. filtrationfilter
  5. washwash the solid with ethanol and ether

Sources & evidence

ORD record
ord-e2191dd56f2446eeb0103dd94f1827d4
Source dataset
uspto-grants-1981_10
Patent number
US04297355

Linked notes

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