2-Thiophenecarbonyl chloride → HCID 10228566, compound

HRID 2416919Notes

Reaction equation

HRID 2416919 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][CH2:6][CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][C:15]([C:17](=[O:26])[N:18]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH3:19])=[CH:16][C:11]=2[N:10]=[C:9]1[NH2:27])[CH3:2].[S:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[C:34](Cl)=[O:35]>N1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][CH2:6][CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][C:15]([C:17](=[O:26])[N:18]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH3:19])=[CH:16][C:11]=2[N:10]=[C:9]1[NH:27][C:34]([C:30]1[S:29][CH:33]=[CH:32][CH:31]=1)=[O:35])[CH3:2]

Participants

4

Reactant 2

HCID 789282-Thiophenecarbonyl chlorideHCID 60123571HCID 60123571, compound

Product 1

HCID 10228566HCID 10228566, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of the above amino benzimidazole (0.7 g, 1.8 mmol) in pyridine (10 mL) was added 2-thiophenecarbonyl chloride (0.41 mL, 3.8 mmol). The reaction was complete in 6 h. The pyridine was evaporated and the resulting orange solid was purified by flash chromatography with 1% MeOH/dichloromethane to give the title compound (0.61 g, 67%), m.p. 82-84° C.

Workup

  1. customThe pyridine was evaporated
  2. customthe resulting orange solid was purified by flash chromatography with 1% MeOH/dichloromethane

Sources & evidence

ORD record
ord-a908e503a52f4fe29d220496d2fc9fed
Source dataset
uspto-grants-2004_11
Patent number
US06825219B2

Reaction notes

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