5-Nitrofurfural → HCID 178426085, compound

HRID 1696663Notes

Reaction equation

HRID 1696663 reaction equation
[H-].[Na+].[SH:3][C:4]1[NH:8][C:7]2[C:9]([CH3:14])=[CH:10][C:11]([Cl:13])=[CH:12][C:6]=2[N:5]=1.[N+]([C:18]1[O:22][C:21]([CH:23]=[O:24])=[CH:20][CH:19]=1)([O-])=O>O1CCCC1>[Cl:13][C:11]1[CH:10]=[C:9]([CH3:14])[C:7]2[NH:8][C:4]([S:3][C:18]3[O:22][C:21]([CH:23]=[O:24])=[CH:20][CH:19]=3)=[N:5][C:6]=2[CH:12]=1

Participants

5

Reactant 3

HCID 127745-NitrofurfuralHCID 24758Sodium hydrideHCID 178426086HCID 178426086, compound

Product 1

HCID 178426085HCID 178426085, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Aldehyde intermediate preparation: A mixture of sodium hydride (60% dispersion in mineral oil, 0.304 g, 7.61 mmol) and 2-mercapto-5-chloro-7-methyl-1H-benzimidazole (0.945 g, 4.76 mmol) in 15 ml of tetrahydrofuran is stirred at room temperature for 2 hours. 5-nitro-2-furaldehyde (0.671 g, 4.56 mmol) in 7 ml of tetrahydrofuran is then added dropwise over a 15 minute period and the mixture is stirred for 16 hours at room temperature. The reaction mixture is then concentrated under reduced pressure and the residue is dissolved in 100 ml of ethyl acetate and washed with water (2×30 ml). The organic phase is dried over MgSO4 and concentrated under reduced pressure. The residue is triturated in diisopropylether and pentane and dried under vacuum to yield 911 mg of 5-(5-chloro-7-methyl-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde. Yield=65%. Analytical LC/MS (method B): retention time: 3.67 min., m/z=292.98 (1 Cl, positive ion mode).

Workup

  1. stirringthe mixture is stirred for 16 hours at room temperature
  2. concentrationThe reaction mixture is then concentrated under reduced pressure
  3. dissolutionthe residue is dissolved in 100 ml of ethyl acetate
  4. washwashed with water (2×30 ml)
  5. dry with materialThe organic phase is dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is triturated in diisopropylether
  8. dry with materialpentane and dried under vacuum

Sources & evidence

ORD record
ord-ec4f6a7639054ea58d4392e7376f270c
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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