Sodium cyanoborohydride → 4'-Aminomethyl-biphenyl-2-sulfonic Acid Dimethylaminomethyleneamide

HRID 967435Notes

Reaction equation

HRID 967435 reaction equation
[CH3:1][N:2]([CH:4]=[N:5][S:6]([C:9]1[C:10]([C:15]2[CH:20]=[CH:19][C:18]([CH:21]=O)=[CH:17][CH:16]=2)=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:7])[CH3:3].[BH3-]C#[N:25].[Na+]>CO>[CH3:1][N:2]([CH:4]=[N:5][S:6]([C:9]1[C:10]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][NH2:25])=[CH:17][CH:16]=2)=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:7])[CH3:3]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 54273713N'-(4'-Formyl[1,1'-biphenyl]-2-sulfonyl)-N,N-dimethylmethanimidamide

Product 1

HCID 696522884'-Aminomethyl-biphenyl-2-sulfonic Acid Dimethylaminomethyleneamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.5 g of 4′-formyl-biphenyl-2-sulfonic acid dimethylaminomethyleneamide prepared according to H. Jendralla et al. (Liebigs Ann. 1995, 1253-7) in 15 ml MeOH were treated with 208.6 mg NaCNBH3 and the reaction was stirred for 4 hours at RT. The pH was adjusted to 4.0, the reaction was filtered, the solvent was removed under reduced pressure and the residue was chromatographed on silica gel eluting with a gradient of 10-20% MeOH in DCM.

Workup

  1. filtrationthe reaction was filtered
  2. customthe solvent was removed under reduced pressure
  3. customthe residue was chromatographed on silica gel eluting with a gradient of 10-20% MeOH in DCM

Sources & evidence

ORD record
ord-068c57eb3b7a4315a11827dbf30d94dc
Source dataset
uspto-grants-2005_10
Patent number
US06953857B2

Reaction notes

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