Acetic Anhydride → Ethyl (2-cyano-3-ethoxybut-2-enoyl)carbamate

HRID 544197노트

반응식

[CH2:1]([O:3][C:4]([NH:6][C:7](=[O:11])[CH2:8][C:9]#[N:10])=[O:5])[CH3:2].[C:12](OCC)(OCC)([O:14][CH2:15][CH3:16])[CH3:13].C(OC(=O)C)(=O)C>>[C:9]([C:8](=[C:12]([O:14][CH2:15][CH3:16])[CH3:13])[C:7]([NH:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:11])#[N:10]

참가 물질

반응물 3

HCID 7918Acetic Anhydride

HCID 23112N-Cyanoacetylethylcarbamate

HCID 66221Triethyl orthoacetate

생성물 1

HCID 53396675Ethyl (2-cyano-3-ethoxybut-2-enoyl)carbamate

실험 절차

Following the method of Example 1, N-ethoxycarbonylcyanoacetamide is heated with triethyl orthoacetate and acetic anhydride to give α-cyano-β-ethoxy-β-methyl-N-ethoxycarbonylacrylamide, which in turn is reacted with 2,4,6-trichlorophenylhydrazine. The resulting compound α-cyano-β-methyl-β-(2,4,6-trichlorophenylhydrazino)-N-ethoxycarbonylacrylamide (m.p.=183°-184°) is cyclized, yielding 5-cyano-6-methyl-1-(2,4,6-trichloroanilino)-2,4-pyrimidinedione, m.p.=>305°.

출처 및 근거

ORD 기록: ord-473c5f9b32ac4f409144c44c796a2f75
출처 데이터셋: uspto-grants-1984_05
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US04448961

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