Sodium hydride → HCID 87972741, compound

HRID 1761034Notes

Reaction equation

HRID 1761034 reaction equation
[H-].[Na+].[SH:3][C:4]1[NH:5][C:6]2[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:7]=2[N:8]=1.[O:15](C(OC(C)(C)C)=O)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=O>O1CCCC1.CO>[CH3:14][O:13][C:11]1[CH:10]=[CH:9][C:7]2[N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:15])[C:4](=[S:3])[N:5]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:15])[C:6]=2[CH:12]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 90495Di-tert-butyl dicarbonateHCID 178488032HCID 178488032, compound

Product 1

HCID 87972741HCID 87972741, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

NaH (60% in oil) (5.55 g; 138 mmol) is added in small portions at 10° C., with stirring, to a solution of 2-mercapto-5-methoxybenzimidazole (10 g; 55.5 mmol) in solution in 400 ml of tetrahydrofuran under argon. The reaction mixture is then stirred for 30 minutes at 0° C., and then BOC2O (26.64 g; 122 mmol) is added in one go. Stirring of the reaction mixture is then carried out for 18 hours at ambient temperature. The reaction mixture is diluted with methanol, filtered over Celite and then concentrated to dryness. The residue obtained is subsequently taken up in a 1/1 mixture of petroleum ether/isopropyl ether. The solid which precipitates is then suction-filtered off to yield the title product in the form of a white powder.

Workup

  1. stirringStirring of the reaction mixture
  2. waitis then carried out for 18 hours at ambient temperature
  3. filtrationfiltered over Celite
  4. concentrationconcentrated to dryness
  5. customThe residue obtained
  6. customThe solid which precipitates
  7. filtrationis then suction-filtered off

Sources & evidence

ORD record
ord-0f054bb0a8fc45749ea22c4a12dc1199
Source dataset
uspto-grants-2005_01
Patent number
US06846833B2

Reaction notes

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