Nitromethane → HCID 123928403, compound

HRID 1509227Notes

Reaction equation

HRID 1509227 reaction equation
CC(C)([O-])C.[K+].[N+:7]([CH3:10])([O-:9])=[O:8].[C:11]([O:15][C:16](=[O:44])[NH:17][C:18]1([C:22]2[CH:27]=[CH:26][C:25]([C:28]3[C:33]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[CH:32][C:31]([N+:40]([O-:42])=[O:41])=[C:30](Cl)[N:29]=3)=[CH:24][CH:23]=2)[CH2:21][CH2:20][CH2:19]1)([CH3:14])([CH3:13])[CH3:12].[NH4+].[Cl-]>CS(C)=O>[C:11]([O:15][C:16](=[O:44])[NH:17][C:18]1([C:22]2[CH:27]=[CH:26][C:25]([C:28]3[C:33]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[CH:32][C:10]([N+:7]([O-:9])=[O:8])=[C:30]([CH2:31][N+:40]([O-:42])=[O:41])[N:29]=3)=[CH:24][CH:23]=2)[CH2:19][CH2:20][CH2:21]1)([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 6375NitromethaneHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 87326920Tert-butyl(1-(4-(6-chloro-5-nitro-3-phenylpyridin-2-yl)phenyl)cyclobutyl)carbamate

Product 1

HCID 123928403HCID 123928403, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of potassium tert-butoxide (468 mg, 4.17 mmol) in dry DMSO (20 ml) was slowly added nitromethane (225 ul, 4.17 mmol) under nitrogen. The resulting mixture was stirred for 15 min at room temperature before tert-butyl(1-(4-(6-chloro-5-nitro-3-phenylpyridin-2-yl)phenyl)cyclobutyl)carbamate (1 g, 2.08 mmol) was added. The resulting mixture was stirred for 1 hour at room temperature. A saturated solution of NH4Cl was added and the mixture was extracted with AcOEt (3×50 ml). The combined organic phases were washed with water (3×20 ml), dried over Na2SO4 and concentrated to dryness under reduced pressure. The resulting residue was used directly without purification. 1H NMR (500 MHz, CDCl3): 8.60 (1H, s), 7.44-7.35 (7H, m), 7.30-7.28 (2H, m), 6.21 (2H, s), 5.09 (1H, s), 2.52-2.20 (4H, m), 2.00-1.95 (1H, m), 1.79-1.65 (1H, m), 1.40-1.10 (9H, br).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with AcOEt (3×50 ml)
  3. washThe combined organic phases were washed with water (3×20 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe resulting residue was used directly without purification

Sources & evidence

ORD record
ord-c1e2852c79bd4e3181bebc6146e20223
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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