Triethylamine → N-tert.-butyl-2-dimethylaminocarbonyl-5-propionylamino-benzenesulfonamide

HRID 581667Notes

Reaction equation

HRID 581667 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:16]([N:18]([CH3:20])[CH3:19])=[O:17])=[C:6]([S:8]([NH:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])=[O:9])[CH:7]=1.[C:21](Cl)(=[O:24])[CH2:22][CH3:23].C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[C:12]([NH:11][S:8]([C:6]1[CH:7]=[C:2]([NH:1][C:21](=[O:24])[CH2:22][CH3:23])[CH:3]=[CH:4][C:5]=1[C:16]([N:18]([CH3:20])[CH3:19])=[O:17])(=[O:9])=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 152405445-Amino-n-tert.-butyl-2-dimethylaminocarbonylbenzenesulfonamide

Product 1

HCID 15240547N-tert.-butyl-2-dimethylaminocarbonyl-5-propionylamino-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

0.85 g of 5-amino-N-tert.-butyl-2-dimethylaminocarbonyl-benzenesulfonamide (Example e) is dissolved in 3.5 ml of DMF at 0° C., and 0.28 g of propionyl chloride and 0.50 ml of triethylamine are added. After the mixture has been stirred at 5° C. for 1 hour, it is taken up in ethyl acetate and washed successively with dilute hydrochloric acid and water. After the mixture has been dried over MgSO4 and the organic phase has been concentrated, 0.60 g of a highly viscous substance, which is employed in subsequent reactions without further purification (Example k), is obtained.

Workup

  1. washwashed successively with dilute hydrochloric acid and water
  2. dry with materialAfter the mixture has been dried over MgSO4
  3. concentrationthe organic phase has been concentrated
  4. custom0.60 g of a highly viscous substance, which is employed in subsequent reactions without further purification (Example k)
  5. customis obtained

Sources & evidence

ORD record
ord-37ce9e29a2e84ad6ae31cc3f6f6559d5
Source dataset
uspto-grants-1999_07
Patent number
US05922646

Reaction notes

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