Hydrochloric Acid → HCID 21265517, compound

HRID 566192Notes

Reaction equation

HRID 566192 reaction equation
C([O:4][C:5]1[C:6]([Br:25])=[CH:7][C:8]([F:24])=[C:9]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]([CH3:22])[C:12]2=[O:23])[CH:10]=1)C=C.O.Cl.C(N(CC)[C:31]1[CH:36]=CC=C[CH:32]=1)C>>[CH2:36]([C:10]1[C:5]([OH:4])=[C:6]([Br:25])[CH:7]=[C:8]([F:24])[C:9]=1[N:11]1[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[N:13]([CH3:22])[C:12]1=[O:23])[CH:31]=[CH2:32]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7061N,N-DiethylanilineHCID 21265564HCID 21265564, compound

Product 1

HCID 21265517HCID 21265517, compound

Procedure

3-(5-Allyloxy-4-bromo-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (3.17 g) was dissolved in N,N-diethylaniline (11 ml) and allowed to react at 210° C. for 2.5 hours. After the completion of the reaction, the reaction solution was poured into water, and diluted hydrochloric acid was added thereto for acidification. It was extracted with ethyl acetate, washed with water, and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off, and the resulting oily substance was purified by chromatography on silica gel (ethyl acetate:n-hexane=1:2 v/v) to obtain the objective 3-(2-allyl-4-bromo-6-fluoro-3-hydroxyphenyl)-1-methyl-6-trifluor-omethyl-2,4(1H,3H)-pyrimidinedione (2.57 g).

Workup

  1. customto react at 210° C. for 2.5 hours
  2. customAfter the completion of the reaction
  3. additionwas added
  4. extractionIt was extracted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationEthyl acetate was distilled off
  8. customthe resulting oily substance was purified by chromatography on silica gel (ethyl acetate:n-hexane=1:2 v/v)

Sources & evidence

ORD record
ord-524b563271cf4ba8b533253a3437cfbf
Source dataset
uspto-grants-2001_01
Patent number
US06174839B1

Reaction notes

Loading…