Sodium Carbonate → HCID 178449977, compound

HRID 1927860Notes

Reaction equation

HRID 1927860 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-fdc3ca98ae9a4b0ea60c40b479d3e88f
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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