Triethylamine → HCID 11820223, compound

HRID 2399707Notes

Reaction equation

HRID 2399707 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH:12]1[CH:16]=[CH:15][N:14]=[N:13]1.C(N(CC)CC)C>C(#N)C>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][N:12]2[CH:16]=[CH:15][N:14]=[N:13]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 660114-Nitrobenzyl bromideHCID 178418936HCID 178418936, compound

Product 1

HCID 11820223HCID 11820223, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Nitrobenzylbromide (25.4 g, 0.12 mol) was added to a solution of 1H-1,2,3-triazole (8.12 g, 0.12 mol) and triethylamine (11.88 g, 0.12 mol) in anhydrous acetonitrile. The mixture was refluxed for 1 h, cooled to room temperature and the precipitated NEt3. HBr filtered off. The solvent was removed under vacuum and the residue chromatographed through silica gel eluting with CH2Cl2 (100) to CH2Cl2 /MeOH (95.5) to give 2-products. The more polar product was identified as the title-1-isomer (13 g, 54%); mp 114°-116° C. δ (250 MHz, CDCl3) 5.72 (2H, s, CH2), 7.38 (2H, d, J=9 Hz, Ar--H), 7.64 (1H, s, Ar--H), 7.78 (1H, s, Ar--H), 8.18 (2H, d, J=9 Hz, Ar--H). The less polar, minor isomer was identified as the 2-alkylation product (2.25 g, 9%), mp 112°-113° C. δ (250 MHz, CDCl3) 5.72 (2H, s, CH2), 7.40 (2H, d, J=9 Hz, Ar--H), 7.66 (2H, s, Ar--H), 8.18 (2H, d, J=9 Hz, Ar--H).

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. filtrationHBr filtered off
  3. customThe solvent was removed under vacuum
  4. customthe residue chromatographed through silica gel eluting with CH2Cl2 (100) to CH2Cl2 /MeOH (95.5)
  5. customto give 2-products

Sources & evidence

ORD record
ord-1964d99d4d12407ca9df294e7eb22bd1
Source dataset
uspto-grants-1995_09
Patent number
US05451588

Reaction notes

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