Hydrochloric Acid → HCID 178444959, compound

HRID 1609289Notes

Reaction equation

HRID 1609289 reaction equation
[NH:1]1[C:5]([CH:6]([O:8][C:9]2[CH:10]=[C:11]([CH:20]=[CH:21][CH:22]=2)[O:12][C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[NH2:15])[CH3:7])=[N:4][N:3]=[N:2]1.C(N(CC)CC)C.[CH2:30]([O:36][C:37]1[CH:45]=[CH:44][C:40]([C:41](Cl)=[O:42])=[CH:39][CH:38]=1)[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].Cl>C(Cl)Cl.C1C=CC=CC=1>[NH:4]1[C:5]([CH:6]([O:8][C:9]2[CH:10]=[C:11]([CH:20]=[CH:21][CH:22]=2)[O:12][C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[NH:15][C:41](=[O:42])[C:40]2[CH:39]=[CH:38][C:37]([O:36][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:45][CH:44]=2)[CH3:7])=[N:1][N:2]=[N:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 170235Benzoyl chloride, 4-(hexyloxy)-HCID 178466631HCID 178466631, compound

Product 1

HCID 178444959HCID 178444959, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent

Procedure

In 30 ml of methylene chloride were dissolved 2.1 g of 2-[3-[1-(1H-tetrazol-5-yl)ethoxy]phenoxy]aniline and 2.2 g of triethylamine, followed by dropwise addition of a solution of 1.7 g of 4-hexyloxybenzoyl chloride in benzene with ice-cooling and stirring. The mixture was stirred at room temperature overnight and refluxed for 1 hour. To the reaction mixture was added ice-water and after the mixture was acidified with diluted hydrochloric acid, the methylene chloride layer was separated. The methylene chloride solution was dried over magnesium sulfate and concentrated and the oily residue was subjected to silica gel column chromatography using chloroform-methanol (100:1) as the eluent to give 2.2 g of the title compound as a light yellow oil.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature overnight
  3. temperaturerefluxed for 1 hour
  4. customthe methylene chloride layer was separated
  5. dry with materialThe methylene chloride solution was dried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3e963d16433042aeab9b5a885ea80189
Source dataset
uspto-grants-1995_03
Patent number
US05399703

Reaction notes

Loading…