Chloroacetone → HCID 70544758, compound

HRID 2057374Notes

Reaction equation

HRID 2057374 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[N:9]=[C:10]1[NH:14][CH2:13][CH2:12][NH:11]1.Cl[CH2:16][C:17](=O)[CH3:18].C(N(CC)CC)C>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[N:9]1[C:10]2=[N:11][CH2:12][CH2:13][N:14]2[C:17]([CH3:18])=[CH:16]1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 8471TriethylamineHCID 178419368HCID 178419368, compound

Product 1

HCID 70544758HCID 70544758, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture consisting of 9.6 gm (0.03 mol) of 2-(2,6-dibromophenyl-imino)-imidazoline, 2.6 ml (110% of the stoichiometrically required amount) of chloroacetone, 3 ml of triethylamine and 30 ml of absolute toluene was heated in a closed tube at 150° C. for 17 hours. Thereafter, the toluene phase was decanted, and the residue was dissolved in dilute hydrochloric acid. The resulting solution was fractionally extracted with ether at stepwisely increasing pH values (addition of 2 N sodium hydroxide). The thin-layer chromatographically pure ethereal fractions were combined, dried over anhydrous calcium sulfate and evaporated in vacuo, leaving 1.65 gm (15.4% of theory) of the compound of the formula ##STR9## which had a melting point of 144°-147° C.

Workup

  1. customThereafter, the toluene phase was decanted
  2. dissolutionthe residue was dissolved in dilute hydrochloric acid
  3. extractionThe resulting solution was fractionally extracted with ether
  4. temperatureat stepwisely increasing
  5. additionpH values (addition of 2 N sodium hydroxide)
  6. dry with materialdried over anhydrous calcium sulfate
  7. customevaporated in vacuo
  8. customleaving 1.65 gm (15.4% of theory) of the compound of the formula ##STR9## which

Sources & evidence

ORD record
ord-ee021848e7e142bab6c3beace5b3122d
Source dataset
uspto-grants-1980_07
Patent number
US04210659

Reaction notes

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