1-(Bromomethyl)-2,4,5-trichlorobenzene → 4,6-Diamino-1,2-dihydro-1-(2,4,5-trichlorophenylmethoxy)-2,2-dimethyl-1,3,5-triazine hydrobromide

HRID 1463286Notes

Reaction equation

HRID 1463286 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]([OH:9])[C:4]([CH3:11])([CH3:10])[N:3]=1.[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([Cl:20])=[CH:15][C:14]=1[CH2:21][Br:22]>CN(C)C=O>[BrH:22].[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]([O:9][CH2:21][C:14]2[CH:15]=[C:16]([Cl:20])[C:17]([Cl:19])=[CH:18][C:13]=2[Cl:12])[C:4]([CH3:11])([CH3:10])[N:3]=1

Participants

4

Reactant 2

HCID 139449891-(Bromomethyl)-2,4,5-trichlorobenzeneHCID 190899224,6-Diamino-1,2-dihydro-1-hydroxy-2,2-dimethyl-1,3,5-triazine

Product 1

HCID 190899624,6-Diamino-1,2-dihydro-1-(2,4,5-trichlorophenylmethoxy)-2,2-dimethyl-1,3,5-triazine hydrobromideYield 63.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.6 gram (0.004 mole) of 4,6-diamino-1,2-dihydro-1-hydroxy-2,2-dimethyl-1,3,5-triazine and 1.6 grams (0.006 mole) of 2,4,5-trichlorophenylmethyl bromide in 5 ml of dimethylformamide was stirred in a closed reaction vessel during about an 18 hour period. After this time the reaction mixture was concentrated under reduced pressure to a residual solid. The solid was washed with 50 ml of acetone. The dried solid was recrystallized from 125 ml of water, yielding 1.1 grams of 4,6-diamino-1,2-dihydro-1-(2,4,5-trichlorophenylmethoxy)-2,2-dimethyl-1,3,5-triazine hydrobromide, m.p. 247°-248° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. concentrationAfter this time the reaction mixture was concentrated under reduced pressure to a residual solid
  2. washThe solid was washed with 50 ml of acetone
  3. customThe dried solid was recrystallized from 125 ml of water

Sources & evidence

ORD record
ord-6afc7322422c4e7c9b5bf97f48a838e5
Source dataset
uspto-grants-1994_04
Patent number
US05300503

Reaction notes

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