4-Chlorobenzenesulfonyl chloride → HCID 131711316, compound

HRID 26969Notes

Reaction equation

HRID 26969 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1>C(Cl)(Cl)Cl>[ClH:27].[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([S:34]([N:18]([CH2:17][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][CH2:9][CH2:8][CH2:7][N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)[CH2:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)(=[O:36])=[O:35])=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 73984-Chlorobenzenesulfonyl chloride2×HCID 21322756N-[[2-[3-(4-Morpholinyl)propoxy]phenyl]methyl]benzeneethanamine

Product 1

HCID 131711316HCID 131711316, compoundYield 172%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

N-[[2-[3-(4-Morpholinyl)propoxy]phenyl]methyl]benzeneethanamine (14 g, see Example 31C) is reacted with 9.2 g of p-chlorobenzenesulfonyl chloride in 130 ml of chloroform. A solution of the amine in chloroform is added dropwise at 10°-15° C. to a stirred solution of the p-chlorobenzenesulfonyl chloride in chloroform. After the addition, the solution is stirred for 1 hour at room temperature and maintained for about 1 hour at room temperature. The chloroform is evaporated, and the residue is rubbed under ether. The resulting solid is taken up in acetonitrile, diluted with ether, rubbed and stored at a reduced temperature for several days, yielding 21.2 g of material, melting point 156°-158° C. Recrystallization from 130 ml of isopropanol yields 17 g of the title compound, melting point 163°-165° C.

Workup

  1. additionAfter the addition
  2. temperaturemaintained for about 1 hour at room temperature
  3. customThe chloroform is evaporated
  4. additiondiluted with ether
  5. waitstored at a reduced temperature for several days

Sources & evidence

ORD record
ord-6a2ae106d0574082b4ecd76b30eaf3d8
Source dataset
uspto-grants-1979_04
Patent number
US04151354

Reaction notes

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