Sodium Hydroxide → HCID 72187789, compound

HRID 515143Notes

Reaction equation

HRID 515143 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+].[F:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26]Br>C1C=CC=CC=1.O1CCCC1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1.O>[CH2:1]([S:3][C:4]1[CH:12]=[C:11]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[CH:10]=[C:9]([CH3:19])[C:5]=1[C:6]([NH:8][CH2:26][C:25]1[CH:28]=[CH:29][CH:30]=[C:23]([F:22])[CH:24]=1)=[O:7])[CH3:2]

Participants

8

Reactant 3

HCID 14798Sodium HydroxideHCID 680073-Fluorobenzyl bromideHCID 866997242-Ethylsulfanyl-6-methyl-4-morpholin-4-yl-benzamide

Product 1

HCID 72187789HCID 72187789, compoundYield 16%

Reagents, catalysts & solvents 4

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 241BenzeneSolventHCID 962WaterSolventHCID 22633675Benzene tetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-ethylsulfanyl-6-methyl-4-morpholin-4-yl-benzamide (0.26 g, 0.92 mmol) in benzene-tetrahydrofuran (1:1) (20 ml) are added tetrabutylammonium hydrogensulfate (0.031 g, 0.091 mmol) and 50% sodium hydroxide solution (8 ml) at RT. The reaction mixture is heated to 80° C. and 3-fluorobenzyl bromide (0.14 ml of a 2M solution in benzene, 0.28 mmol) is added. The reaction mixture is stirred at 80° C. for 15 min. After completion of the reaction (monitored by TLC), the reaction mixture is diluted with water (15 ml) and extracted with ethyl acetate (15×3 ml). The organic layer is washed with water (20 ml), brine (15 ml), dried over anhydrous sodium sulfate and evaporated to get the crude product, which is purified by column chromatography (silica gel, 25% ethyl acetate/hexane) to yield 2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-6-methyl-4-morpholin-4-yl-benzamide (example 1) (0.06 g, 0.15 mmol, 16%). [M+H]+ 389.1.

Workup

  1. customAfter completion of the reaction (monitored by TLC)
  2. extractionextracted with ethyl acetate (15×3 ml)
  3. washThe organic layer is washed with water (20 ml), brine (15 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customto get the crude product, which
  7. customis purified by column chromatography (silica gel, 25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-feb3e339a00a4bd58b1d2ba57e451550
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

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