Hydrochloric Acid → HCID 12151215, compound

HRID 2415036Notes

Reaction equation

HRID 2415036 reaction equation
[C:1]([C:3]1[C:8]([I:9])=[C:7]([C:10]([F:13])([F:12])[F:11])[N:6]=[C:5]([S:14][CH3:15])[N:4]=1)#[N:2].O.[N-:17]=[N+:18]=[N-:19].[Na+].Cl>C(O)(C)C.[Br-].[Zn+2].[Br-]>[I:9][C:8]1[C:3]([C:1]2[N:17]=[N:18][NH:19][N:2]=2)=[N:4][C:5]([S:14][CH3:15])=[N:6][C:7]=1[C:10]([F:12])([F:11])[F:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 33557Sodium AzideHCID 12151210HCID 12151210, compound

Product 1

HCID 12151215HCID 12151215, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 3776IsopropanolSolvent

Procedure

4-Cyano-5-iodo-2-methylthio-6-trifluoromethylpyrimidine (0.50 g) was dissolved in isopropanol (5 ml) and added water (10 ml), sodium azide (0.19 g) and zinc bromide (0.16 g) with stirring in room temperature. The mixture was refluxed for 3 hr and then cooled to room temperature and then added 3N-HCl to acidify. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine, respectively and dried over magnesium sulfate. The solvent was removed under reduced pressure to give 5-iodo-2-methylthio-4-(2H-tetrazol-5-yl)-6-trifluoromethyl-pyrimidine (0.5 g) as colorless crystalline solid, mp 196-200° C.

Workup

  1. temperatureThe mixture was refluxed for 3 hr
  2. temperaturecooled to room temperature
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water and brine
  5. dry with materialrespectively and dried over magnesium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6c935487842f4442ac1944079666deaa
Source dataset
uspto-grants-2004_11
Patent number
US06818631B1

Reaction notes

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