Hexamethylenetetramine → 1-[(3-Phenyl-5-isoxazolyl)methyl]-3,5,7-triaza-1-azoniaadamantane bromide

HRID 2420121Notes

Reaction equation

HRID 2420121 reaction equation
[Br:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]=1.[CH2:14]1[N:19]2[CH2:20][N:21]3[CH2:23][N:17]([CH2:18]2)[CH2:16][N:15]1[CH2:22]3>C(Cl)(Cl)Cl>[Br-:1].[C:8]1([C:5]2[CH:4]=[C:3]([CH2:2][N+:15]34[CH2:16][N:17]5[CH2:23][N:21]([CH2:20][N:19]([CH2:18]5)[CH2:14]3)[CH2:22]4)[O:7][N:6]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 4101Hexamethylenetetramine2×HCID 27487965-(Bromomethyl)-3-phenylisoxazole

Product 1

HCID 203397401-[(3-Phenyl-5-isoxazolyl)methyl]-3,5,7-triaza-1-azoniaadamantane bromide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 90 g. portion of the product of Example 1 was dissolved in 1.5 l. of chloroform and 70 g. of hexamethylenetetramine was added. The mixture was stirred at reflux temperature for 4 hours, and was filtered hot. The solids were dried under vacuum to obtain 143 g. of impure product, m.p. 159°-160°, which contained about 93 percent product and 7 percent hexamethylenetetramine.

Workup

  1. temperatureat reflux temperature for 4 hours
  2. filtrationwas filtered hot
  3. customThe solids were dried under vacuum
  4. customto obtain 143 g

Sources & evidence

ORD record
ord-d8d3a5867f7a43cc9b282d2db864c159
Source dataset
uspto-grants-1978_08
Patent number
US04109002

Reaction notes

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