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Thionyl Chloride → 2-(1,2,3,4-tetrahydroquinolin-1-yl)-4H-pyrido[3,2-e]-1,3-thiazin-4-one monohydrate

HRID 367178
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HRID 367178 반응식
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[N-:15]=[C:16]=[S:17].[NH4+].Br[C:20]1[CH:21]=[C:22]2[C:27](=[C:28](Br)[CH:29]=1)[NH:26][CH2:25][CH2:24][CH2:23]2>CC(C)=O.CN(C=O)C>[OH2:5].[N:26]1([C:16]2[S:17][C:2]3[N:10]=[CH:9][CH:8]=[CH:7][C:3]=3[C:4](=[O:6])[N:15]=2)[C:27]2[C:22](=[CH:21][CH:20]=[CH:29][CH:28]=2)[CH2:23][CH2:24][CH2:25]1
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참가 물질

7

반응물 4

HCID 24386Thionyl ChlorideHCID 762582-Chloronicotinic acidHCID 232876446,8-Dibromo-1,2,3,4-tetrahydroquinolineHCID 178514171HCID 178514171, 화합물

생성물 1

HCID 232876382-(1,2,3,4-tetrahydroquinolin-1-yl)-4H-pyrido[3,2-e]-1,3-thiazin-4-one monohydrate수율 84.3%

시약·촉매·용매 2

HCID 180
Acetone
용매
2회
HCID 6228Dimethylformamide용매

실험 절차

The reaction procedure of Example 57 was followed except that 1.339 g (8.5 mmol) of 2-chloronicotinic acid, 13 ml of thionyl chloride, two droplets of DMF, 680 mg of ammonium isothiocyanate, 13 ml of acetone, 2.473 g of 6,8-dibromo-1,2,3,4-tetrahydroquinoline and 8 ml of acetone were used. The product was then recrystallized from a mixture of ethanol and hexane to obtain 2.244 g of 2-(1,2,3,4-tetrahydroquinolin-1-yl)-4H-pyrido[3,2-e]-1,3-thiazin-4-one monohydrate.

후처리

  1. customThe reaction procedure of Example 57
  2. customThe product was then recrystallized from a mixture of ethanol and hexane

출처 및 근거

ORD 기록
ord-8c653e1fff9c4f9fa8e057e880f88459
출처 데이터셋
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06133258

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