Water → 2-Methyl-propane-2-sulfinic acid [(2-amino-5-bromo-phenyl)-(4-chloro-phenyl)-methyl]-amide

HRID 1497714Notes

Reaction equation

HRID 1497714 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)=[N:10][S:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[O:12].O.[BH4-].[Na+]>C1COCC1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[CH:9]([NH:10][S:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[O:12])[C:17]1[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 1234860542-Methyl-propane-2-sulfinic acid (2-amino-5-bromo-phenyl)-(4-chloro-phenyl)-methyleneamide

Product 1

HCID 1176205182-Methyl-propane-2-sulfinic acid [(2-amino-5-bromo-phenyl)-(4-chloro-phenyl)-methyl]-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-Methyl-propane-2-sulfinic acid (2-amino-5-bromo-phenyl)-(4-chloro-phenyl)-methyleneamide (6.82 g, 0.02 mmol) dissolved in THF (196 mL) and H2O (4 mL) is added NaBH4 (1.57 g, 0.04 mol) at 0° C. The mixture is stirred at RT. The mixture is quenched with MeOH and H2O, MeOH and THF is removed. The mixture is extracted with ethyl acetate, dried over NaSO4 and concentrated. This provides the desired compound which is used without further purification.

Workup

  1. customThe mixture is quenched with MeOH and H2O, MeOH and THF
  2. customis removed
  3. extractionThe mixture is extracted with ethyl acetate
  4. dry with materialdried over NaSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-00647f19ed204231a127b7ca0cc59d2d
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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