Ethanol → HCID 178452725, compound

HRID 730402Notes

Reaction equation

HRID 730402 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[C:12]#[N:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:18][OH:19].CCO.C(=O)([O-])[O-].[K+].[K+]>O>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:11]([C:12](=[NH:13])[NH:18][OH:19])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 12129277tert-Butyl (3-cyanophenyl)carbamate

Product 1

HCID 178452725HCID 178452725, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A 5 L round bottom flask equipped with an overhead stirrer, and 500 mL addition funnel was charged with 3-(t-butyloxycarbonylamino)benzonitrile (264.4 g, 1.21 mol), hydroxylamine hydrochloride (294.6 g, 4.24 mol) and 95% EtOH (1 L). The resulting suspension was treated with a solution of potassium carbonate (711.8 g, 5.15 mol) in water (1 L) and the suspension heated to 60° C. The reaction was followed by TLC and HPLC for starting material consumption to completion. The reaction mixture was then cooled to ambient temperature the organic layer was separated and concentrated to approximately 500 mL, then diluted with water (1 L). The resulting precipitate was collected by vacuum filtration and dried to yield the title compound as an off white solid.

Workup

  1. customA 5 L round bottom flask equipped with an overhead stirrer, and 500 mL addition funnel
  2. custommaterial consumption to completion
  3. temperatureThe reaction mixture was then cooled to ambient temperature the organic layer
  4. customwas separated
  5. concentrationconcentrated to approximately 500 mL
  6. additiondiluted with water (1 L)
  7. filtrationThe resulting precipitate was collected by vacuum filtration
  8. customdried

Sources & evidence

ORD record
ord-1c6f96da80214a1a9e84ff6f5cec11c5
Source dataset
uspto-grants-2009_09
Patent number
US07582753B2

Reaction notes

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