Triphenylphosphine → N-benzylaminosulfonamide

HRID 1735939Notes

Reaction equation

HRID 1735939 reaction equation
[S:1]([NH2:5])([NH2:4])(=[O:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:25]([CH:27]([CH2:31][CH2:32][CH2:33][CH3:34])[C:28]([O-])=O)C.[Na+]>C1C=CC=CC=1.C(OCC)(=O)C>[CH2:28]([NH:4][S:1]([NH2:5])(=[O:3])=[O:2])[C:27]1[CH:25]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 82267SulfamideHCID 23672331Sodium 2-ethylhexanoate

Product 1

HCID 12354987N-benzylaminosulfonamideYield 64%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

The condensed sulfamide having an allyloxycarbonyl protecting group obtained as Sample No. 3 of Example 1 is dissolved in benzene (10 vol.), and triphenylphosphine (0.3 Eq.), sodium 2-ethylhexanoate (1.5 Eq.) in ethyl acetate, and palladium tetrakistriphenylphosphine (0.02 Eq.) are added thereto successively. The mixture is stirred at room temperature for 30 minutes. The reaction mixture is diluted with ethyl acetate, washed with water, dried, and concentrated in vacuo. The residue is recrystallized from toluene to give benzylsulfamide having the same physical constants as that obtained in Reference Example 1. Pale yellow crystals. Yield: 64%.

Workup

  1. customobtained as Sample No
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue is recrystallized from toluene

Sources & evidence

ORD record
ord-b9d9e9714487402284a77792be89d894
Source dataset
uspto-grants-1996_07
Patent number
US05539102

Reaction notes

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