Pyridine → HCID 20263705, compound

HRID 464038Notes

Reaction equation

HRID 464038 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]1[NH:7][N:6]=[N:5][N:4]=1.[C:10](Cl)(=[O:26])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].N1C=CC=CC=1>C(#N)C>[C:10]([N:4]1[C:3]([C:2]([F:9])([F:8])[F:1])=[N:7][N:6]=[N:5]1)(=[O:26])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8206Palmitoyl chlorideHCID 178506305HCID 178506305, compound

Product 1

HCID 20263705HCID 20263705, compoundYield 43.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
5 °C

Procedure

6.9 g of 5-trifluoromethyl-1,2,3,4-tetrazole and 13.7 g of palmitoyl chloride were dissolved in 100 ml of acetonitrile while cooling with ice and to the solution was added dropwise 4.5 ml of pyridine over a period of about 10 minutes. After the completion of the dropwise addition, the mixture was stirred at about 5° C. for 30 minutes and then at room temperature for 1 hour, and to the mixture was added dropwise about 100 ml of ice water. The crystals thus-deposited were collected by filtration to obtain 8.2 g of 1-hexadecanoyl-5-trifluoromethyl-1,2,3,4 -tetrazole. A melting point was 66° to 69° C.

Workup

  1. temperaturewhile cooling with ice and to the solution
  2. additionAfter the completion of the dropwise addition
  3. waitat room temperature for 1 hour
  4. filtrationThe crystals thus-deposited were collected by filtration

Sources & evidence

ORD record
ord-8c5e73afbf9a4faea9e53a36551afd1a
Source dataset
uspto-grants-1985_10
Patent number
US04546075

Reaction notes

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