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

HRID 1583484ノート

反応式

HRID 1583484 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒3 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-61b900aa40bb42e497a84071a87111a8
出典データセット
uspto-grants-1985_11
特許番号
US04552585

反応ノート

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