Phosphorus pentachloride → HCID 68296403, compound

HRID 631871Notes

Reaction equation

HRID 631871 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[C:12]=2[C:21]([NH2:23])=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)(Cl)Cl.C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:21]([C:12]1[C:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C:18]=2[CH:19]=[CH:20][C:11]=1[NH:10][S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:8])=[O:9])#[N:23]

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 68296406HCID 68296406, compound2×

Product 1

HCID 68296403HCID 68296403, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Benzenesulfonylamino-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid amide (Intermediate 2, 1.2 g) was dissolved in dry DCM (20 mL) and phosphorous pentachloride (0.9 g) was added. The mixture was stirred for 3 hours then saturated aqueous sodium hydrogencarbonate was added carefully and the products were extracted into ethyl acetate. The organic solution was dried with magnesium sulfate, filtered and the solvent was removed by evaporation. The residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane. The fractions containing the desired product were combined and the solvent was evaporated to give the title compound as an off-white solid.

Workup

  1. extractionthe products were extracted into ethyl acetate
  2. dry with materialThe organic solution was dried with magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed by evaporation
  5. customThe residue was purified by chromatography on silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane
  7. additionThe fractions containing the desired product
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-61610417cac24ead97a9e22b89bd09e1
Source dataset
uspto-grants-2016_04
Patent number
US09321740B2

Reaction notes

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