Sodium Carbonate → HCID 178449977, compound

HRID 1989137Notes

Reaction equation

HRID 1989137 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[N:22])[N:16]=2)[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:24][OH:25].C(=O)([O-])[O-].[Na+].[Na+]>CCO.O>[C:1]([NH:5][S:6]([C:9]1[CH:10]=[C:11]([C:15]2[N:16]=[C:17]([C:21]([NH:24][OH:25])=[NH:22])[CH:18]=[CH:19][CH:20]=2)[CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 60209334HCID 60209334, compound

Product 1

HCID 178449977HCID 178449977, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-tert-butyl-3-(6-cyano-pyridin-2-yl)-benzenesulfonamide (example B.13) (1.03 g, 3.27 mmol), hydroxylamine hydrochloride (794 mg, 11.4 mmol) and sodium carbonate (692 mg, 6.53 mmol) in EtOH (20 ml) and water (20 ml) was stirred under argon atmosphere at 100° C. for 2 h. The EtOH was evaporated, the mixture was diluted with water and stirred for 1 h at 0° C. The crude product was filtered and dried in HV to give the pure title compound as a white solid (850 mg, 75%). MS (ISP) 349.3 [(M+H)+].

Workup

  1. customThe EtOH was evaporated
  2. additionthe mixture was diluted with water
  3. stirringstirred for 1 h at 0° C
  4. filtrationThe crude product was filtered
  5. customdried in HV

Sources & evidence

ORD record
ord-464f87a12cea4522ad4c82818db7ef55
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

Loading…