Hydrochloric Acid → HCID 18619151, compound

HRID 1862341Notes

Reaction equation

HRID 1862341 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[CH:4][C:3]=1[OH:22].[CH2:23]([O:30][C:31]1[C:32](Cl)=[N:33][S:34][N:35]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[CH2:23]([O:30][C:31]1[C:32]([O:22][C:3]2[CH:4]=[C:5]([N:9]3[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:18])([F:19])[F:17])[N:11]([CH3:20])[C:10]3=[O:21])[C:6]([F:8])=[CH:7][C:2]=2[Cl:1])=[N:33][S:34][N:35]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 112677571-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedioneHCID 18619208HCID 18619208, compound

Product 1

HCID 18619151HCID 18619151, compoundYield 28.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 0.60 g of 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenol and 0.50 g of 4-benzyloxy-3-chloro-1,2,5-thiadiazole in 8 ml of dimethyl sulfoxide, 0.25 g of potassium carbonate was added, and stirred for 30 minutes at 50° C., and for 3 hours at 100° C. The reaction solution was poured into dilute hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water, then, saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.27 g of 4-benzyloxy-3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-1,2,5-thiadiazole (purity: 44%)

Workup

  1. waitfor 3 hours at 100° C
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialsaturated saline, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9756d8107af1438caa35911242435caf
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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