Triethylamine → HCID 178443160, compound

HRID 903304Notes

Reaction equation

HRID 903304 reaction equation
[CH2:1]([O:15][C:16]1[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=1[C:18](=[O:21])[CH2:19]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[NH:26]1[CH:30]=[N:29][N:28]=[N:27]1.C(N(CC)CC)C>C(#N)C>[NH:26]1[C:30]([CH2:19][C:18]([C:17]2[CH:22]=[CH:23][CH:24]=[CH:25][C:16]=2[O:15][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:21])=[N:29][N:28]=[N:27]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20516628HCID 20516628, compoundHCID 178418441HCID 178418441, compound

Product 1

HCID 178443160HCID 178443160, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 14.6 g of o-tetradecyloxyphenacylbromide in 75 ml of acetonitrile was added a solution of 2.8 g of tetrazole and 4.0 g of triethylamine in 75 ml of acetonitrile. The reaction mixture was stirred at reflux temperature for 2 hours then evaporated to dryness. The residue was dissolved in chloroform and the organic layer washed with water, dried over magnesiumsulfate, filtered and evaporated to give the crude compound. Recrystallisation from petrol (b.p. 60°-80° C.) gave the acetophenone derivative as a fine white powder. Yield: 12.7 g; m.p. 67° to 69° C.

Workup

  1. temperatureat reflux temperature for 2 hours
  2. customthen evaporated to dryness
  3. dissolutionThe residue was dissolved in chloroform
  4. washthe organic layer washed with water
  5. dry with materialdried over magnesiumsulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto give the crude compound
  9. customRecrystallisation from petrol (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-1c134ee3be2a42ecaedc855b2a855812
Source dataset
uspto-grants-1980_10
Patent number
US04226934

Reaction notes

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