Thionyl Chloride → 4-Oxo-4H-chromene-3-carbonitrile

HRID 2048959

반응식

HRID 2048959 반응식
O1C2C(=CC=CC=2)C(=O)C(C(O)=O)=C1.S(Cl)(Cl)=O.[O:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](=[O:29])[C:21]([C:30]([NH2:32])=O)=[CH:20]1>CN(C)C=O>[C:30]([C:21]1[C:22](=[O:29])[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:19][CH:20]=1)#[N:32]

참가 물질

5

반응물 3

HCID 24386Thionyl Chloride2회HCID 181620Chromone-3-carboxylic acidHCID 12200777HCID 12200777, 화합물2회

생성물 1

HCID 5212984-Oxo-4H-chromene-3-carbonitrile수율 75%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The present invention concerns a novel method of preparing these 3-cyanochromones from chromone-3-carboxylic acids. The reaction mechanism of the present invention may best be described by the following reaction scheme: ##STR4## Referring to the reaction scheme, chromone-3-carboxylic acid is initially converted to the acyl chloride by treating with thionyl chloride as disclosed in U.S. Pat. No. 3,849,446 to Von Strandtmann, et al., issued Nov. 19, 1974. The acyl chloride is then converted to the corresponding chromone-3-carboxamide, as disclosed in U.S. Pat. No. 3,862,143. The critical feature of the present invention is the further dehydration of the chromone-3-carboxamide with thionyl chloride in N,N-dimethylformamide to give the desired 3-cyanochromone in a high yield of at least 75%. Generally, a molar excess of thionyl chloride and a 30-40 molar excess of N,N-dimethylformamide are employed.

후처리

  1. customThe reaction mechanism of the present invention may best be described by the following reaction scheme

출처 및 근거

ORD 기록
ord-4528319ddc564a6fbbcc2626b18674de
출처 데이터셋
uspto-grants-1980_04
특허 번호
US04196128

연결된 노트

불러오는 중…