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

HRID 541060Notes

Reaction equation

HRID 541060 reaction equation
[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

Participants

6

Reactant 3

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

Product 2

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-693a29988b6646a79c5c0f451f916e7b
Source dataset
uspto-grants-2014_10
Patent number
US08871946B2

Reaction notes

Loading…