Hexamethylenetetramine → Hexamethylenetetramine

HRID 1414207Notes

Reaction equation

HRID 1414207 reaction equation
[CH2:1]1[N:6]2[CH2:7][N:8]3[CH2:10][N:4]([CH2:5]2)[CH2:3][N:2]1[CH2:9]3.[C:11]([O-:21])(=[O:20])[C@H:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[OH:13]>C(C(C)=O)C>[CH2:1]1[N:6]2[CH2:7][N:8]3[CH2:10][N:4]([CH2:5]2)[CH2:3][N:2]1[CH2:9]3.[C:11]([O-:21])(=[O:20])[CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[OH:13]

Participants

5

Reactant 2

HCID 4101HexamethylenetetramineHCID 5460348(S)-Mandelate

Product 2

HCID 4101HexamethylenetetramineHCID 3839223Mandelate ion

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

To a boiling suspension of 160 ml. of methyl ethyl ketone containing 23.0 g. (0.165 mole) of methenamine is slowly added a hot suspension of 25 g. (0.16 mole) of l-mandelate acid in 60 ml. of methyl ethyl ketone. The heat source is removed. The solution is stirred to room temperature, then cooled in an ice-water bath. White crystals are collected by filtration, washed with a small amount of cold methyl ethyl ketone, followed by anhydrous ether, and dried at 50° C. in vacuum for 4.5 hours to obtain methenamine levo-mandelate. mp. 133.5°-135.5° C [α]D20 -63.3° (C = 3,H2O)

Workup

  1. additionTo a boiling suspension of 160 ml
  2. additiona hot suspension of 25 g
  3. customThe heat source is removed
  4. temperaturecooled in an ice-water bath
  5. filtrationWhite crystals are collected by filtration
  6. washwashed with a small amount of cold methyl ethyl ketone
  7. customdried at 50° C. in vacuum for 4.5 hours

Sources & evidence

ORD record
ord-6a6f4c1e48814c608b26746177085d14
Source dataset
uspto-grants-1977_01
Patent number
US04001231

Reaction notes

Loading…