Propylamine → 5-Chloro-6-n-propylsulfamoyl-1-indanone

HRID 65934Notes

Reaction equation

HRID 65934 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].C(N(CC)CC)C.[Cl:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][C:21]=1[S:22](Cl)(=[O:24])=[O:23])[C:18](=[O:26])[CH2:17][CH2:16]2>CC(C)=O>[Cl:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][C:21]=1[S:22](=[O:23])(=[O:24])[NH:4][CH2:1][CH2:2][CH3:3])[C:18](=[O:26])[CH2:17][CH2:16]2

Participants

5

Reactant 3

HCID 7852PropylamineHCID 8471TriethylamineHCID 221190346-chloro-3-oxo-2,3-dihydro-1H-indene-5-sulfonyl chloride

Product 1

HCID 227563895-Chloro-6-n-propylsulfamoyl-1-indanone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 1.95 g (33 mmoles) of n-propylamine and 3.04 g (30 mmoles) of triethylamine in 50 ml of acetone is added to a solution of 7.95 g (30 mmoles) of 5-chloro-6-chlorosulfonyl-1-indanone in 50 ml of acetone, and the whole is stirred for 6 hours at room temperature, thereafter for 1 hour at boiling temperature. The solution is largely concentrated, 200 ml of water are added, and the mixture is then acidified with 2N hydrochloric acid to a pH of 2. The precipitate is filtered off with suction and washed with water. The product melts at 122° to 123° C.

Workup

  1. waitfor 1 hour at boiling
  2. concentrationThe solution is largely concentrated
  3. addition200 ml of water are added
  4. filtrationThe precipitate is filtered off with suction
  5. washwashed with water

Sources & evidence

ORD record
ord-1b2fe95f2bff4408ab484d41b09ebfc3
Source dataset
uspto-grants-1978_12
Patent number
US04129656

Reaction notes

Loading…