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Thionyl Chloride → 2-(5-nitro-2-thienyl)-1H-benzimidazole

HRID 541060
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HRID 541060 반응식
[N+:1]([C:4]1[S:8][C:7]([C:9]2[NH:13][C:12]3[CH:14]=[CH:15][CH:16]=[C:17](C(O)=O)[C:11]=3[N:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)(Cl)=[O:22].[NH2:25][CH:26]([CH3:36])[CH:27]([C:29]1[CH:34]=[CH:33][C:32](Cl)=[CH:31][CH:30]=1)[OH:28]>O1CCCC1>[N+:1]([C:4]1[S:8][C:7]([C:9]2[NH:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[N:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH:22][CH2:36][CH:26]([NH-:25])[CH:27]([OH:28])[C:29]1[CH:34]=[CH:33][C:32]([N+:1]([O-:3])=[O:2])=[CH:31][CH:30]=1
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참가 물질

6

반응물 3

HCID 24386Thionyl ChlorideHCID 1526614-ChloronorephedrineHCID 669844772-(5-nitro-2-thienyl)-1H-benzimidazole-4-carboxylic acid

생성물 2

HCID 145927722-(5-nitro-2-thienyl)-1H-benzimidazoleHCID 86658971N-(1-hydroxymethyl-2-p-nitrophenylhydroxyethyl)amide

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

1.0 g of 2-(5-nitro-2-thienyl)-1H-benzimidazole-4-carboxylic acid is added into 15 ml of thionyl chloride; and to heat and reflux it for 60 minutes. After end of the reaction, 2-amino-1-p-chlorophenyl-1-propanol (1.1 eq) is dissolved into tetrahydrofuran, and then drop acyl chloride to the above tetrahydrofuran mixture under stirring at the room temperature and then filter inorganic salt, evaporate the solvent to dry, and then isolate the mixture through column chromatography to obtain 2-(5-nitro-2-thienyl)-1H-benzimidazole-4-(N-(1-hydroxymethyl-2-p-nitrophenylhydroxyethyl)amide. The yield is about 92%.

후처리

  1. temperatureand to heat
  2. temperaturereflux it for 60 minutes
  3. filtrationfilter inorganic salt
  4. customevaporate the solvent
  5. customto dry
  6. customisolate the mixture through column chromatography

출처 및 근거

ORD 기록
ord-693a29988b6646a79c5c0f451f916e7b
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08871946B2

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