Dichloromethane → 4-[[3-(p-Chlorophenyl)propyl]methylamino]benzoic acid, ethyl ester

HRID 1154354Notes

Reaction equation

HRID 1154354 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][NH:11][C:12]2[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.Cl[CH2:24]Cl.CS(F)(=O)=O.[OH-].[Na+]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][N:11]([CH3:24])[C:12]2[CH:13]=[CH:14][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:21][CH:22]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11207Methanesulfonyl FluorideHCID 14798Sodium HydroxideHCID 13079692Ethyl 4-{[3-(4-chlorophenyl)propyl]amino}benzoate

Product 1

HCID 442788874-[[3-(p-Chlorophenyl)propyl]methylamino]benzoic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.0 g. of ethyl 4-[3-(p-chlorophenyl)propylamino]benzoate, 20 ml. of dry dichloromethane and 2.5 ml. of methane sulfonyl fluoride is stirred for 18 hours, then refluxed for 3 hours. The solution is poured into 30 ml. of water and adjusted to pH 10 with 10N sodium hydroxide. The dichloromethane layer is separated and saved. The aqueous layer is extracted with two 20 ml. portions of dichloromethane. The organic layers are combined, washed with 10 ml. of water, dried over anhydrous magnesium sulfate, and evaporated to yield 1.80 g. of the desired product as a light yellow oil.

Workup

  1. additionA mixture of 1.0 g
  2. temperaturerefluxed for 3 hours
  3. additionThe solution is poured into 30 ml
  4. customThe dichloromethane layer is separated
  5. extractionThe aqueous layer is extracted with two 20 ml
  6. washwashed with 10 ml
  7. dry with materialof water, dried over anhydrous magnesium sulfate
  8. customevaporated
  9. customto yield 1.80 g

Sources & evidence

ORD record
ord-fece9dcecc9d4259b9318987b022f9b8
Source dataset
uspto-grants-1984_12
Patent number
US04489094

Reaction notes

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