Oxalyl chloride → N,N'-Dimethoxy-N,N'-dimethyloxamide

HRID 1386683ノート

反応式

HRID 1386683 の反応式
Cl.[CH3:2][NH:3][O:4][CH3:5].[C:6](Cl)(=[O:10])[C:7](Cl)=[O:8]>C(Cl)Cl.N1C=CC=CC=1>[CH3:2][N:3]([O:4][CH3:5])[C:7]([C:6]([N:3]([CH3:2])[O:4][CH3:5])=[O:10])=[O:8]

参加物

4

反応物 2

HCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

生成物 1

HCID 3287678N,N'-Dimethoxy-N,N'-dimethyloxamide収率 69%

試薬・触媒・溶媒 1

HCID 21875418Pyridine methylene chloride溶媒

反応条件

温度
-78 °C

実験手順

A mixture of 48.0 g (0.49 mol) of N,O-dimethylhydroxylamine HCl in 250 mL of 3:2 v/v CH2Cl2/pyridine was cooled to −78° C. and treated with 17.4 mL (0.2 mol) of oxalyl chloride maintaining the internal temperature at less than −70° C. The resulting mixture was allowed to warm to rt and stirred for 20 h. The reaction was quenched with 250 mL of sat'd NaCl and the quenched mixture was extracted with 3×400 mL of CH2Cl2. The extracts were combined, dried over MgSO4 and concentrated. Recrystallization from 250 mL of methyl t-butyl ether afforded 24.28 g (69%) of the title compound: 1H NMR (500 MHz) δ 3.25 (s, 6H), 3.75 (s, 6H).

後処理

  1. temperatureto warm to rt
  2. customThe reaction was quenched with 250 mL of sat'd NaCl
  3. extractionthe quenched mixture was extracted with 3×400 mL of CH2Cl2
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customRecrystallization from 250 mL of methyl t-butyl ether

出典と根拠

ORDレコード
ord-f466d204ef794186b88c2e89609aaeed
出典データセット
uspto-grants-2001_07
特許番号
US06265434B1

反応ノート

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