Triethylamine → HCID 178513410, compound

HRID 1506853Notes

Reaction equation

HRID 1506853 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10]C(C#N)[O:8][C:7]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[C:6]=2[CH:25]=1.Cl.[NH2:27][OH:28].C([N:31]([CH2:34][CH3:35])CC)C>CO>[OH:28][NH:27][C:34]([CH:35]1[O:8][C:7]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:6]2[CH:25]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:10]1)=[NH:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 89907420HCID 89907420, compound

Product 1

HCID 178513410HCID 178513410, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 500 mg 6-chloro-4,4-dicyclohexyl-4H-benzo[1,3]dioxine-2-carbonitrile, 204 mg hydroxylamine hydrochloride and 0.41 ml triethylamine in 7 ml methanol was refluxed for 8 hours. The solvent was removed in vacuo, the residue dissolved in EtOAc and washed with water. The aqueous phase was extracted with EtOAc, the combined organic phases were washed with brine and dried over MgSO4. After removal of the solvent, the crude product was directly used in the next step. Yield: 540 mg.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in EtOAc
  3. washwashed with water
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washthe combined organic phases were washed with brine
  6. dry with materialdried over MgSO4
  7. customAfter removal of the solvent

Sources & evidence

ORD record
ord-3ed49d45d77e436c94852bbf1dfa9414
Source dataset
uspto-grants-2015_12
Patent number
US09221784B2

Reaction notes

Loading…