Phosphorus oxychloride → HCID 178463280, compound

HRID 540161Notes

Reaction equation

HRID 540161 reaction equation
[O:1]=[S:2]1(=[O:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5]([C:13](=O)[CH3:14])[CH2:4][CH2:3]1.P(Cl)(Cl)(Cl)=O.[NH2:22][C:23]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:24]=1[C:25]#[N:26].C(=O)(O)[O-].[Na+]>ClCCl.O>[O:1]=[S:2]1(=[O:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5](/[C:13](=[N:22]/[C:23]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:24]=2[C:25]#[N:26])/[CH3:14])[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 2427782-Amino-5-methylbenzonitrileHCID 516892Sodium BicarbonateHCID 712551431-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)ethanone

Product 1

HCID 178463280HCID 178463280, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)ethanone (6.0 g, 25.0 mmol) in dry dichloromethane (100 mL) was added phosphorus oxychloride (2.5 mL, 27.3 mmol) at 10° C. After being stirred for 20 minutes at room temperature, a solution of 2-amino-5-methylbenzonitrile (3.3 g, 25.0 mmol) in dry dichloromethane (40 mL) was added and the resulting suspension was heated under reflux for 24 hours. After being cooled to room temperature, the reaction mixture was diluted with water (50 mL), basified with a saturated aqueous solution of sodium bicarbonate to about pH 8. The separated aqueous layer was extracted with dichloromethane (100 mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 16% ethyl acetate in petroleum ether) to give 1.5 g of the product as a white solid.

Workup

  1. temperaturethe resulting suspension was heated
  2. temperatureunder reflux for 24 hours
  3. temperatureAfter being cooled to room temperature
  4. extractionThe separated aqueous layer was extracted with dichloromethane (100 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography on silica gel (eluting with 16% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-99ad294eff2d436691dd1d9a9370843a
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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