Methyl Bromide → HCID 13590774, compound

HRID 1249352Notes

Reaction equation

HRID 1249352 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][CH:10]2[CH:15]3[O:16][C:17]4[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=4[O:19][CH:14]3[CH2:13][CH2:12][CH2:11]2)[CH2:3][CH2:2]1.[CH3:24][Br:25]>CC(C)=O>[Br-:25].[CH2:13]1[CH:14]2[CH:15]([O:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[O:19]2)[CH:10]([O:9][CH2:8][CH2:7][N+:4]2([CH3:24])[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 6323Methyl BromideHCID 13590769HCID 13590769, compound

Product 1

HCID 13590774HCID 13590774, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In an autoclave, 900 g (2.82 moles) of the amino ether of Example 3 were dissolved in 3 liters of acetone, and 535.6 g (5.64 moles) of methyl bromide were added. After crystallisation had started, the mixture was left with stirring for 2 hours at room temperature. After being filtered and rinsed with acetone, the solid formed was resuspended in petroleum ether, stirring, filtered, dried under vacuum and then recrystallised in a minimum quantity of the mixture diisopropyl ether/isopropanol (7:3). There were thus obtained 1000 g of the title-compound of melting point 155° C., having the elementary analysis:

Workup

  1. customAfter crystallisation
  2. waitthe mixture was left
  3. filtrationAfter being filtered
  4. washrinsed with acetone
  5. customthe solid formed
  6. stirringstirring
  7. filtrationfiltered
  8. customdried under vacuum
  9. customrecrystallised in a minimum quantity of the mixture diisopropyl ether/isopropanol (7:3)

Sources & evidence

ORD record
ord-83c201e0264b411d8240d5f718188db3
Source dataset
uspto-grants-1986_12
Patent number
US04631277

Reaction notes

Loading…