Water → HCID 131734225, compound

HRID 1497700Notes

Reaction equation

HRID 1497700 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][CH:20]=[CH:19][CH:18]=1)=[N:10][S:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[O:12].[BH4-].[Na+].O>C1COCC1.O>[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:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 123869272HCID 123869272, compound

Product 1

HCID 131734225HCID 131734225, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
-50 °C

Procedure

2-Methyl-propane-2-sulfinic acid (2-amino-5-bromo-phenyl)-phenyl-methyleneamide (70 g, 184 mol) is dissolved in 98:2 THF/H2O (800 mL) and was cooled to −50° C. Then NaBH4 (17.5 g, 462 mol) is added and the mixture is stirred at room temperature overnight. Then H2O is added and concentrated and extracted with EtOAc. The organic layer is concentrated to give product.

Workup

  1. concentrationconcentrated
  2. extractionextracted with EtOAc
  3. concentrationThe organic layer is concentrated
  4. customto give product

Sources & evidence

ORD record
ord-c6c0af7bccc44d7a865932069032ae98
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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