Benzaldehyde → HCID 22255974, compound

HRID 1611740Notes

Reaction equation

HRID 1611740 reaction equation
[BH4-].[Na+].[NH2:3][C:4]1[C:8]([C:9]#[N:10])=[C:7]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6][N:5]=1.O.O.O.C([O-])(=O)C.[Na+].[CH:26](=O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(O)(=O)C.O.C(O)C.C(OCC)(=O)C>[CH2:26]([NH:3][C:4]1[C:8]([C:9]#[N:10])=[C:7]([NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[S:6][N:5]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

9

Reactant 4

HCID 240BenzaldehydeHCID 4311764Sodium borohydrideHCID 14171368HCID 14171368, compoundHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 22255974HCID 22255974, compoundYield 65.1%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium borohydride (4.12 g, 1.09.1 mmol) was added portion wise to a mixture of 3-amino-5-phenylamino-isothiazole-4-carbonitrile (1.57 g, 7.27 mmol), sodium acetate trihydrate (2.97 g, 21.81 mmol) and benzaldehyde (0.74 ml, 7.27 mmol) in acetic acid (2.3 ml), water (9 ml) and ethanol (7 ml) at 0° C. The solution was stirred at ambient temperature for 30 minutes, and then diluted with ethyl acetate (EtOAc) (55 ml). The organic layer was washed with a 10% solution of sodium hydroxide (3×35 ml) and brine (35 ml), dried and evaporated to give an oil, which was purified on silica gel (hexane/EtOAc, 1:1) to afford a solid (1.45 g, 65%).

Workup

  1. washThe organic layer was washed with a 10% solution of sodium hydroxide (3×35 ml) and brine (35 ml)
  2. customdried
  3. customevaporated
  4. customto give an oil, which
  5. customwas purified on silica gel (hexane/EtOAc, 1:1)

Sources & evidence

ORD record
ord-cea6045fb6af4634a4cf61d26114b466
Source dataset
uspto-grants-2006_01
Patent number
US06989451B2

Reaction notes

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