Methanamine, N-methoxy-, hydrochloride (1:1) → 2-chloro-4-[(N-methoxy-N-methylamino)carbonylamino]phenylmethyl bromide

HRID 1583484Notes

Reaction equation

HRID 1583484 reaction equation
Cl.[CH3:2][O:3][NH:4][CH3:5].C(=O)(O)[O-].[Na+].[Br:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]=[C:20]=[O:21])=[CH:15][C:14]=1[Cl:22]>C(OCC)C.O>[Cl:22][C:14]1[CH:15]=[C:16]([NH:19][C:20]([N:4]([O:3][CH3:2])[CH3:5])=[O:21])[CH:17]=[CH:18][C:13]=1[CH2:12][Br:11]

Participants

6

Reactant 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 135572724-Bromomethyl-3-chlorophenylisocyanate

Product 1

HCID 135572732-chloro-4-[(N-methoxy-N-methylamino)carbonylamino]phenylmethyl bromideYield 28%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
0 °C

Procedure

A stirred solution of 58.3 grams (0.597 mole) of O,N-dimethylhydroxylamine hydrochloride in 400 ml of diethyl ether was cooled to 0° C. and a slurry of 50.2 grams (0.597 mole) of sodium bicarbonate in 50 ml of water was added. Upon completion of addition the reaction mixture stirred at 0° C. for one hour, then a solution of 147.2 grams (0.597 mole) of 4-bromomethyl-3-chlorophenylisocyanate in 100 ml of diethyl ether was added. During the addition, additional diethyl ether was added to the reaction mixture to promote stirring. Upon completion of addition the reaction mixture was stirred for an additional one hour, then was filtered. The filtrate was dried with magnesium sulfate and refiltered. The filtrate was concentrated under reduced pressure to a solid residue. The solid was triturated with ethanol to remove a yellow color. The solid was collected by filtration to give 51.5 grams of 2-chloro-4-[(N-methoxy-N-methylamino)carbonylamino]phenylmethyl bromide.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. additionwas added to the reaction mixture
  3. stirringto promote stirring
  4. additionUpon completion of addition the reaction mixture
  5. stirringwas stirred for an additional one hour
  6. filtrationwas filtered
  7. dry with materialThe filtrate was dried with magnesium sulfate
  8. concentrationThe filtrate was concentrated under reduced pressure to a solid residue
  9. customThe solid was triturated with ethanol
  10. customto remove a yellow color
  11. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-61b900aa40bb42e497a84071a87111a8
Source dataset
uspto-grants-1985_11
Patent number
US04552585

Reaction notes

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