Dimethylformamide → 3-(4-chlorobenzylidene)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one

HRID 1198444

반응식

HRID 1198444 반응식
[NH:1]1[C:6](=[O:7])[CH2:5][S:4][C:3]2[CH:8]=[CH:9][C:10]3[C:15]([C:2]1=2)=[CH:14][CH:13]=[CH:12][CH:11]=3.[Cl:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1.C[O-].[Na+].CN(C)C=O>O>[Cl:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[C:5]2[S:4][C:3]3[CH:8]=[CH:9][C:10]4[C:15]([C:2]=3[NH:1][C:6]2=[O:7])=[CH:14][CH:13]=[CH:12][CH:11]=4)=[CH:19][CH:18]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 77264-ChlorobenzaldehydeHCID 10942334Sodium MethoxideHCID 138234521H-Naphtho[2,1-b][1,4]thiazin-2(3H)-one

생성물 1

HCID 537645223-(4-chlorobenzylidene)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one수율 52.8%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one (5.17 g), 4-chlorobenzaldehyde (5.62 g), sodium methoxide (1.73 g) and dimethylformamide (80 ml) is refluxed for 4.5 hours. After cooling, the reaction mixture is poured into water and the resulting precipitate is separated by filtration, washed and dried and then is recrystallized from tetrahydrofuran-n-hexane to give 3-(4-chlorobenzylidene)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one (4.28 g). M.p. 277°-279° C.

후처리

  1. temperatureis refluxed for 4.5 hours
  2. temperatureAfter cooling
  3. customthe resulting precipitate is separated by filtration
  4. washwashed
  5. customdried
  6. customis recrystallized from tetrahydrofuran-n-hexane

출처 및 근거

ORD 기록
ord-74230d890d7741afbc348924db4e9c4f
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05281592

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