Formic Acid → HCID 2822888, compound

HRID 1954774Notes

Reaction equation

HRID 1954774 reaction equation
[NH2:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)[C:6](=[O:16])[N:5]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:4](=[O:24])[CH:3]=1.C(O)=O.N([O-])=O.[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH:40]([NH2:42])=O>>[CH2:17]([N:5]1[C:4](=[O:24])[C:3]2[NH:42][CH:40]=[N:1][C:2]=2[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)[C:6]1=[O:16])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 5

HCID 284Formic AcidHCID 713FormamideHCID 24489Sodium DithioniteHCID 2822886HCID 2822886, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 2822888HCID 2822888, compound

Conditions

Temperature
100 °C

Procedure

A mixture of 6-amino-3-benzyl-1-(3-methoxyphenyl)uracil (5.52 g), formic acid (3.2 ml) and sodium nitrite (1.45 g) in formamide (130 ml) was gradually heated up to 100° C. with stirring. Sodium dithionite (4.83 g) was then added in portions over a period of 10 min, the temperature being held at 100° C. The temperature was then raised to 190° C. and the mixture stirred at this temperature for 30 min. It was allowed to cool then extracted into chloroform. The chloroform solution was extracted into 2M sodium hydroxide solution and this washed with ether. The aqueous layer was acidified with concentrated hydrochloric acid to give a solid which was filtered off and washed with water. Recrystallisation from ethanol provided the title compound (1.55 g).

Workup

  1. custombeing held at 100° C
  2. temperatureThe temperature was then raised to 190° C.
  3. stirringthe mixture stirred at this temperature for 30 min
  4. temperatureto cool
  5. extractionthen extracted into chloroform
  6. extractionThe chloroform solution was extracted into 2M sodium hydroxide solution
  7. washthis washed with ether
  8. customto give a solid which
  9. filtrationwas filtered off
  10. washwashed with water
  11. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-77a773534e324cbb84565c10771a0195
Source dataset
uspto-grants-2000_09
Patent number
US06124288

Reaction notes

Loading…