Sodium Hydroxide → HCID 72187844, compound

HRID 515156Notes

Reaction equation

HRID 515156 reaction equation
[CH2:1]([S:3]([C:6]1[CH:14]=[C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:12]=[C:11]([CH3:21])[C:7]=1[C:8]([NH2:10])=[O:9])(=[O:5])=[O:4])[CH3:2].[OH-].[Na+].[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1>C1C=CC=CC=1.O1CCCC1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH:10][C:8](=[O:9])[C:7]2[C:11]([CH3:21])=[CH:12][C:13]([N:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)=[CH:14][C:6]=2[S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])=[CH:27][CH:26]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 86699732HCID 86699732, compound

Product 1

HCID 72187844HCID 72187844, compoundYield 115%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 8028TetrahydrofuranSolventHCID 22633675Benzene tetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution 2-(ethylsulfonyl)-6-methyl-4-morpholin-4-yl-benzamide (0.27 g, 0.88 mmol) in benzene-tetrahydrofuran (1:1) (10 ml) are added tetrabutylammonium hydrogensulfate (0.03 g, 0.09 mmol) and 15% sodium hydroxide solution (8 ml) at RT. 4-Chlorobenzyl bromide (0.083 g, 0.40 mmol) in tetrahydrofuran (1.5 ml) is added and the reaction mixture is slowly heated to 70° C. The reaction mixture is stirred at 70° C. for additional 25 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, 15% acetone/hexane) to yield N-[(4-chlorophenyl)-methyl]-2-(ethylsulfonyl)-6-methyl-4-morpholin-4-yl-benzamide (example 8) (0.20 g, 0.46 mmol, 74%). [M+H]+ 437.1.

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, 15% acetone/hexane)

Sources & evidence

ORD record
ord-d14e48719d6a4836a1af24a995cfe2ac
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

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