Triethylamine → HCID 68908400, compound

HRID 2061320Notes

Reaction equation

HRID 2061320 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH2:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.Cl[P:23]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O1CCCC1>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH2:14])(=[O:12])=[O:13])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[C:30]1([PH:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66180ChlorodiphenylphosphineHCID 20547764-butylbenzene-1-sulfonamide

Product 1

HCID 68908400HCID 68908400, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Commercially available 4-butylbenzene-1-sulfonamide (9.376 mole, 1 eq) was dissolved in tetrahydrofuran (20 mL) and triethylamine (25 mmole), leading to a clear colorless solution. Distilled chlorobisphenylphosphine (9.376 mmole, 1.0 eq) was added dropwise under strong magnetic stirring at room temperature. The suspension was left to stir overnight at room temperature. The suspension was then filtered under argon atmosphere and the resulting clear solution was evaporated to a white solid. The product was redissolved in 10 mL of diethylether leading to a clear solution. 10 mL of pentane were added dropwise to the solution causing a white solid to crash out. The organic layer was syringed out, and the white solid obtained was washed twice with 10 mL of pentane. The product was filtered over a short silica gel column with dichloromethane as eluent. The product was obtained as white solid. The product was characterized by 1H, 31P, 13C NMR.

Workup

  1. waitThe suspension was left
  2. stirringto stir overnight at room temperature
  3. filtrationThe suspension was then filtered under argon atmosphere
  4. customthe resulting clear solution was evaporated to a white solid
  5. dissolutionThe product was redissolved in 10 mL of diethylether leading to a clear solution
  6. addition10 mL of pentane were added dropwise to the solution
  7. customthe white solid obtained
  8. washwas washed twice with 10 mL of pentane
  9. filtrationThe product was filtered over a short silica gel column with dichloromethane as eluent
  10. customThe product was obtained as white solid

Sources & evidence

ORD record
ord-f17c87c2e3be4fa7b111c4f627c9585d
Source dataset
uspto-grants-2012_10
Patent number
US08283276B2

Reaction notes

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