Triethylamine → HCID 21802382, compound

HRID 1656017Notes

Reaction equation

HRID 1656017 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:19][CH:20]=O)([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.F[B-](F)(F)F.C([N+]1C2C=CC=CC=2OC=1Cl)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N+:19]#[C-:20])([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27242402-Chloro-3-ethylbenzoxazolium tetrafluoroborateHCID 21802383HCID 21802383, compound

Product 1

HCID 21802382HCID 21802382, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 0.40 g (1.3 mmols) of N-[2-(4-chlorophenyl)-1-(1,2,4-triazol-1-yl)-2-hexyl]formamide in 5 mL of methylene chloride under nitrogen was added 0.45 mL (3.26 mmols) of triethylamine. To this mixture was added a slurry of 0.439 g (1.63 mmols) of 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate, which was weighed out under a nitrogen atmosphere, in 5 mL of methylene chloride. The reaction mixture was then allowed to stir at room temperature for 12 hours. The reaction mixture was poured into ice water and extracted with ethyl acetate. The combined organic layers were washed once with 10% hydrochloric acid, brine, and dried over magnesium sulfate. Removal of solvents gave a crude oil which was purified by column chromatography (Merck 60 silica gel, ethyl acetate/hexane) to give 0.20 g (52%) of a clear, colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed once with 10% hydrochloric acid, brine
  3. dry with materialdried over magnesium sulfate
  4. customRemoval of solvents
  5. customgave a crude oil which
  6. customwas purified by column chromatography (Merck 60 silica gel, ethyl acetate/hexane)
  7. customto give 0.20 g (52%) of a clear, colorless oil

Sources & evidence

ORD record
ord-e4719c960f974106af2b92994f759c02
Source dataset
uspto-grants-1993_10
Patent number
US05252594

Reaction notes

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