HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium Hydroxide → 3-Isopropyl-5-bromo-6-(trifluoromethyl)uracil

HRID 1576489
Notes
Print preview

Reaction equation

HRID 1576489 reaction equation
[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[NH:6][C:5]1=[O:15])([CH3:3])[CH3:2].[OH-].[Na+].[Br:18]Br.S(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH:1]([N:4]1[C:9](=[O:10])[C:8]([Br:18])=[C:7]([C:11]([F:12])([F:14])[F:13])[NH:6][C:5]1=[O:15])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24408Bromine2×HCID 112068123-isopropyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedioneHCID 23665763Sodium Bisulfite

Product 1

HCID 215107803-Isopropyl-5-bromo-6-(trifluoromethyl)uracil

Reagents, catalysts & solvents 1

HCID 6212
Chloroform
Solvent
2×

Procedure

3-isopropyl-6-(trifluoromethyl)uracil as prepared in Example 1 (7.4 g., 0.033 mole) was dissolved in a mixture of 0.5N NaOH (0.04 mole) and chloroform (15 ml.). A solution of bromine (5.89 g., .036 mole) in 25 ml. chloroform was added in portions with stirring. After the addition was complete, the reaction mixture was stirred for one-half hour before discharging the bromine color with sodium bisulfite. The layers were separated, and the aqueous layer extracted with fresh chloroform. The combined chloroform extracts were washed with water and then evaporated to dryness leaving 10.1 g. (100%) of white solid residue. One recrystallization from benzene gave a product with a melting point of 146°-150°C. The analytical sample melted at 149°-150°C.

Workup

  1. additionAfter the addition
  2. stirringthe reaction mixture was stirred for one-half hour
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with fresh chloroform
  5. washThe combined chloroform extracts were washed with water
  6. customevaporated to dryness
  7. customleaving 10.1 g
  8. customOne recrystallization from benzene
  9. customgave a product with a melting point of 146°-150°C

Sources & evidence

ORD record
ord-449115f057b54ebf9d89593aa049214b
Source dataset
uspto-grants-1976_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03981715

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes