Hexamethylenetetramine → HCID 20337667, compound

HRID 1395621Notes

Reaction equation

HRID 1395621 reaction equation
[CH2:1]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:25])[CH2:23]Br)=[CH:18][CH:17]=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].C1N2CN3CN(C2)C[N:27]1C3.C(Cl)(Cl)[Cl:37]>>[ClH:37].[CH2:1]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:25])[CH2:23][NH2:27])=[CH:18][CH:17]=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]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6212ChloroformHCID 539946982-Bromo-1-[4-(tetradecyloxy)phenyl]ethan-1-one2×

Product 1

HCID 20337667HCID 20337667, compoundYield 95%

Procedure

88 g of p-tetradecyloxy-ω-bromoacetophenone (stage 2 of compound 29) are dissolved in 320 ml of dried chloroform. 30.4 g of urotropin are added at room temperature. The solution undergoes spontaneous heating. It is stirred for 2 hours at room temperature. The chloroform is distilled off and the solid residue is rubbed with acetone. The crystalline deposit is filtered off under suction and washed repeatedly with acetone. The crude product is then introduced into a solution of 140 ml of concentrated sulphuric acid in 100 ml of ethanol, followed by stirring for 24 hours at room temperature. After filtration under suction, the residue is washed with a mixture of ethanol and concentrated hydrochloric acid (7:1), giving 80 g=95% of p-tetradecyloxy-ω-aminoacetophenone hydrochloride melting at 190°-195° C.

Workup

  1. distillationThe chloroform is distilled off
  2. filtrationThe crystalline deposit is filtered off under suction
  3. washwashed repeatedly with acetone
  4. additionThe crude product is then introduced into a solution of 140 ml of concentrated sulphuric acid in 100 ml of ethanol
  5. stirringby stirring for 24 hours at room temperature
  6. filtrationAfter filtration under suction
  7. washthe residue is washed with a mixture of ethanol and concentrated hydrochloric acid (7:1)

Sources & evidence

ORD record
ord-576c2a364c9a4e2291a8bfab5ab912e4
Source dataset
uspto-grants-1980_05
Patent number
US04204867

Reaction notes

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