Hexamethylenetetramine → 4-(2',6'-Dichlorobenzyl)oxazole

HRID 325950Notes

Reaction equation

HRID 325950 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:3]=1[CH2:4][C:5]([CH:7]=[O:8])=O.[CH2:14]1N2CN3CN(C2)C[N:15]1C3.C([O-])(=O)C.[NH4+]>C(N)=O>[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:3]=1[CH2:4][C:5]1[N:15]=[CH:14][O:8][CH:7]=1

Participants

5

Reactant 3

HCID 4101HexamethylenetetramineHCID 517165Ammonium AcetateHCID 204633232,6-Dichlorobenzylglyoxal

Product 1

HCID 204633054-(2',6'-Dichlorobenzyl)oxazole

Reagents, catalysts & solvents 1

HCID 713FormamideSolvent

Conditions

Temperature
100 °C

Procedure

21.7 g of crude 2,6-dichlorobenzylglyoxal are dissolved in 50 ml of formamide. 7.0 g of hexamethylenetetramine and 30.8 g of ammonium acetate are added and the reaction mixture is stirred at 100° C. for 2 hours, then is evaporated to dryness in vacuo. 200 ml of water are added and the pH of the aqueous phase is adjusted, while stirring, to 2-3 with concentrate hydrochloric acid. The solution is washed with toluene (3×50 ml). The aqueous solution is made alkaline with sodium hydroxide (pH=8-9) and then extracted three times with chloroform (1×100 ml and 2×50 ml). The combined chloroform extracts are washed with water, dried with sodium sulfate and evaporated to dryness. The residue, which consisted of crude product, is used in step (c) below.

Workup

  1. customis evaporated to dryness in vacuo
  2. addition200 ml of water are added
  3. stirringwhile stirring, to 2-3 with concentrate hydrochloric acid
  4. washThe solution is washed with toluene (3×50 ml)
  5. extractionextracted three times with chloroform (1×100 ml and 2×50 ml)
  6. washThe combined chloroform extracts are washed with water
  7. dry with materialdried with sodium sulfate
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-beaca45448a7416f9b2081a7557a3197
Source dataset
uspto-grants-1984_04
Patent number
US04443466

Reaction notes

Loading…