Propylamine → Chlorpropamide

HRID 461424Notes

Reaction equation

HRID 461424 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].[C:5]1(=O)OC(C)C[O:6]1.[CH:12]1[C:17]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:16][CH:15]=[C:14]([Cl:22])[CH:13]=1>CN(C=O)C>[Cl:22][C:14]1[CH:13]=[CH:12][C:17]([S:18]([NH:21][C:5]([NH:4][CH2:1][CH2:2][CH3:3])=[O:6])(=[O:20])=[O:19])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7852PropylamineHCID 7924Propylene CarbonateHCID 668244-Chlorobenzenesulfonamide

Product 1

HCID 2727Chlorpropamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

n-Propylamine (5.9 g., 0.1 mole.) and propylene carbonate (10.2 g., 0.1 mole.) were mixed and heated at 60° over night. To the resulting hydroxypropyl-n-propylcarbomate were added p-chlorobenzene sulfonamide (10.67 g., as sodium salt) and DMF (200 ml.) and the mixture was heated at 120° for 4 hours. After evaporation of the solvent the residue was taken up in water (200 ml.) and the solution adjusted to pH 8 by the addition of acetic acid. Unreacted p-chlorobenzene sulfonamide (2 g.) separated out and was collected. Further adjustment to pH 5 precipitated 1-(4-chloro-benzenesulfonyl)-3-n-propyl-urea (2 g.) whose infrared spectrum was identical with that of an authentic sample.

Workup

  1. temperatureheated at 60° over night
  2. temperaturethe mixture was heated at 120° for 4 hours
  3. customAfter evaporation of the solvent the residue
  4. additionthe solution adjusted to pH 8 by the addition of acetic acid
  5. customUnreacted p-chlorobenzene sulfonamide (2 g.) separated out
  6. customwas collected
  7. customFurther adjustment to pH 5 precipitated 1-(4-chloro-benzenesulfonyl)-3-n-propyl-urea (2 g.) whose

Sources & evidence

ORD record
ord-7c88bc7c4a234c8280312ff4ff0c73a4
Source dataset
uspto-grants-1977_12
Patent number
US04062889

Reaction notes

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