M-Phenylenediamine → N,N'-(m-phenylene)bis citraconamic acid

HRID 2256

반응식

HRID 2256 반응식
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.[C:9]1(=[O:16])[O:15][C:13](=[O:14])[CH:12]=[C:10]1[CH3:11]>CC(C)=O>[C:1]1([NH:8][C:13](=[O:14])/[CH:12]=[C:10](/[CH3:11])\[C:9]([OH:16])=[O:15])[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:13](=[O:14])/[CH:12]=[C:10](/[CH3:11])\[C:9]([OH:15])=[O:16])[CH:2]=1

참가 물질

4

반응물 2

HCID 7935M-PhenylenediamineHCID 12012Citraconic Anhydrides

생성물 1

HCID 22883495N,N'-(m-phenylene)bis citraconamic acid수율 99.9%

시약·촉매·용매 1

HCID 180Acetone용매3회

실험 절차

A 3-liter, 3-neck round bottom flask was charged with 54 g (0.5 mole) of m-phenylenediamine and 500 ml of reagent acetone and flushed with nitrogen. The flask was fitted with a reflux condenser, mechanical stirrer and thermocouple. A dropping funnel containing 112 g (1.0 mole) of citraconic anhydride in 500 ml of reagent acetone was attached and the solution added dropwise over about 1 1/2 hours with stirring as the temperature was allowed to rise to reflux the acetone. The reaction mixture was refluxed for an additional hour, cooled to room temperature and suction filtered to give 166 g of N,N'-(m-phenylene)bis citraconamic acid as shown by NMR analysis, as a tan mustard-colored solid melting at 152°-156° C.

후처리

  1. customflushed with nitrogen
  2. customThe flask was fitted with a reflux condenser, mechanical stirrer
  3. additionthe solution added dropwise over about 1 1/2 hours
  4. temperatureThe reaction mixture was refluxed for an additional hour
  5. filtrationsuction filtered

출처 및 근거

ORD 기록
ord-81e816ae13fd471baa1f76ede4d59949
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728757

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