Pyridine → 4-Chloro-N-[4-(methylthio)phenyl]benzamide

HRID 1896778Notes

Reaction equation

HRID 1896778 reaction equation
[CH3:1][S:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.N1C=CC=CC=1.[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1>ClCCl>[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH:7][C:6]2[CH:8]=[CH:9][C:3]([S:2][CH3:1])=[CH:4][CH:5]=2)=[O:22])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 85014-Chlorobenzoyl chlorideHCID 660384-(Methylthio)aniline

Product 1

HCID 3064824-Chloro-N-[4-(methylthio)phenyl]benzamideYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
12.5 °C

Procedure

To 4-(methylthio)aniline (1 mL, 8.19 mmol) in dichloromethane (20 mL) was added pyridine (2 mL, 24.6 mmol). The resulting solution was cooled to 10-15° C. and 4-chlorobenzoyl chloride (1.14 mL, 9.00 mmol) was added over 5 min. The mixture was stirred at room temperature for 90 min. The precipitate was filtered off, washed with dichloromethane, 1M aqueous sodium hydroxide solution and 1M aqueous hydrochloric acid solution to afford 2.12 g (93%) of the title compound.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with dichloromethane, 1M aqueous sodium hydroxide solution and 1M aqueous hydrochloric acid solution

Sources & evidence

ORD record
ord-6b168b756d3f4157b2bbf933b07e1b15
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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