Sodium Hydroxide → HCID 72187838, compound

HRID 515145Notes

Reaction equation

HRID 515145 reaction equation
[CH2:1]([S:3][C:4]1[CH:12]=[C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:10]=[C:9]([CH3:19])[C:5]=1[C:6]([NH2:8])=[O:7])[CH3:2].[OH-].[Na+].[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=1>C1C=CC=CC=1.O1CCCC1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH:8][C:6](=[O:7])[C:5]2[C:9]([CH3:19])=[CH:10][C:11]([N:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)=[CH:12][C:4]=2[S:3][CH2:1][CH3:2])=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 866997242-Ethylsulfanyl-6-methyl-4-morpholin-4-yl-benzamide

Product 1

HCID 72187838HCID 72187838, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 22633675Benzene tetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-ethylsulfanyl-6-methyl-4-morpholin-4-yl-benzamide (synthesized according to the methods described in sections b) and c) of example 1) (0.20 g, 0.71 mmol) in benzene-tetrahydrofuran (1:1) (16 ml) are added tetrabutylammonium hydrogensulfate (0.024 g, 0.071 mmol) and 50% sodium hydroxide solution (6 ml) at RT. The reaction mixture is heated to 70° C. and 4-chlorobenzyl bromide (0.15 g, 0.71 mmol) is added. The reaction mixture is stirred at 70° C. for 20 min. After completion of the reaction (monitored by TLC), the organic layer is separated and the aqueous layer is extracted with ethyl acetate (2×20 ml). The organic layer is washed with water (20 ml), brine (20 ml), dried over anhydrous sodium sulfate and evaporated to get the crude product, which is purified by column chromatography (silica gel, 28% ethyl acetate/hexane) to yield N-[(4-chlorophenyl)-methyl]-2-ethylsulfanyl-6-methyl-4-morpholin-4-yl-benzamide (example 2) (0.095 g, 0.24 mmol, 50%). [M+H]+ 405.1.

Workup

  1. customAfter completion of the reaction (monitored by TLC)
  2. customthe organic layer is separated
  3. extractionthe aqueous layer is extracted with ethyl acetate (2×20 ml)
  4. washThe organic layer is washed with water (20 ml), brine (20 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. customto get the crude product, which
  8. customis purified by column chromatography (silica gel, 28% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-107606548ba64aac916d03a7c23b8180
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

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