Dimethylformamide → HCID 14461486, compound

HRID 1904747Notes

Reaction equation

HRID 1904747 reaction equation
[H-].[Na+].CN(C=O)C.[S:8]1[C:12]2=[C:13]([CH2:17][S:18][C:19]3[NH:20][C:21]4[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=4[N:23]=3)[N:14]=[CH:15][CH:16]=[C:11]2[CH:10]=[CH:9]1.Cl[C:29]([O:31][CH2:32][CH3:33])=[O:30]>CCOCC.O>[CH2:32]([O:31][C:29]([N:23]1[C:22]2[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=2[N:20]=[C:19]1[S:18][CH2:17][C:13]1[N:14]=[CH:15][CH:16]=[C:11]2[CH:10]=[CH:9][S:8][C:12]=12)=[O:30])[CH3:33]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 14461480HCID 14461480, compound

Product 1

HCID 14461486HCID 14461486, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To 44.0 mg (1.10 mmol) of 60% NaH were added 7 ml of dry DMF and 299.2 mg (1.00 mmol) of 2-[(thieno[2, 3-c]pyridin-7-yl)methylthio]benzimidazole. 1/10 H2O (Ia-1). After stirring for 10 min. at room temperature, the solution was added with 130.2 mg (1.20 mmol) of ClCOOEt and stirred for 30 minutes at room temperature. DMF was evaporated under reduced pressure. Water was added to the residue, and the solution was extracted with CH2Cl2. After drying over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, whereby 381.0 mg of pale greenish yellow cyrstals were obtained. After being subjected to silica gel column chromatography, the crystals were dispersed with 2 ml of ether, followed by filtration and washed with ether, whereby 335.7 mg (Yield : 90.9%) of the objective compound, 1-ethoxycarbonyl-2-[(thieno[2, 3-c]pyridin-7-yl)methylthio]benzimidazole (Ib-1) was obtained as crystals.

Workup

  1. stirringstirred for 30 minutes at room temperature
  2. customDMF was evaporated under reduced pressure
  3. additionWater was added to the residue
  4. extractionthe solution was extracted with CH2Cl2
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure, whereby 381.0 mg of pale greenish yellow cyrstals
  7. customwere obtained
  8. filtrationfollowed by filtration
  9. washwashed with ether, whereby 335.7 mg (Yield : 90.9%) of the objective compound

Sources & evidence

ORD record
ord-c2a828411bd84355bc65f5327ec67ddf
Source dataset
uspto-grants-1989_06
Patent number
US04839365

Reaction notes

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