Sodium Carbonate → HCID 178513243, compound

HRID 1053779Notes

Reaction equation

HRID 1053779 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]#[N:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1.Cl.[NH2:13][OH:14].C([O-])([O-])=O.[Na+].[Na+]>CCO>[OH:14][NH:13][C:10]([C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH:2]=[CH:3][C:4]=2[CH:9]=1)=[NH:11]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 27951841-Benzofuran-5-carbonitrile

Product 1

HCID 178513243HCID 178513243, compoundYield 172.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

Prepared using General Procedure 1. To a flask containing benzofuran-5-carbonitrile (200 mg, 0.73 mmol) was added EtOH (6 mL), hydroxylamine hydrochloride (176.7 mg, 2.54 mmol) and Na2CO3 (154 mg, 1.42 mmol). The mixture was stirred at 75° C. overnight then concentrated, re-dissolved in DCM and washed with NaHCO3. The combined organic layers were dried over Na2SO4, and concentrated to provide 222 mg of crude N-hydroxybenzofuran-5-carboximidamide INT-68 as a white solid which was used directly in the next step without purification. LCMS-ESI (m/z) calculated for C9H8N2O2: 176.2; found 177.1 [M+H]+, tR=0.83 min.

Workup

  1. customPrepared
  2. concentrationthen concentrated
  3. dissolutionre-dissolved in DCM
  4. washwashed with NaHCO3
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1620ed58c85d4ab498dc063ea31d1811
Source dataset
uspto-grants-2016_07
Patent number
US09394264B2

Reaction notes

Loading…