Sodium Hydroxide → HCID 21105604, compound

HRID 2426646Notes

Reaction equation

HRID 2426646 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:23])[C:9](=[O:22])[C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].[Br:32][CH:33]([CH2:37][CH2:38]Cl)[C:34](Br)=[O:35].[OH-].[Na+]>C(#N)C.O>[Br:32][CH:33]1[CH2:37][CH2:38][N:1]([C:2]2[CH:7]=[CH:6][C:5]([N:8]([CH3:23])[C:9](=[O:22])[C:10]3[CH:15]=[CH:14][C:13]([CH:16]4[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]4)=[CH:12][CH:11]=3)=[CH:4][CH:3]=2)[C:34]1=[O:35]

Participants

7

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 24243Trisodium PhosphateHCID 110327461719-99-9HCID 21105617HCID 21105617, compound

Product 1

HCID 21105604HCID 21105604, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

N-(4-Aminophenyl)-4-cyclohexyl-N-methylbenzamide (3.0 g) in acetonitrile (30 ml) was mixed with trisodium phosphate (0.95 g) and, at 0° C., 2-bromo-4-chlorobutyryl bromide (2.9 g) was added. After one hour, a solution of sodium hydroxide (0.85 g) in water (10 ml) was added and the mixture was stirred vigorously at room temperature for 6 hours. The same amount of sodium hydroxide solution was then added, and stirring was continued for 48 hours. The reaction solution was diluted with water and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated. The residue was purified by chromatography on silica gel (mobile phase ethyl acetate/heptane 1:2). This resulted in the product with the molecular weight of 455.40 (C24H27BrN2O2); MS (ESI): 456 (M+H+).

Workup

  1. stirringstirring
  2. waitwas continued for 48 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel (mobile phase ethyl acetate/heptane 1:2)
  7. customThis resulted in the product with the molecular weight of 455.40 (C24H27BrN2O2)

Sources & evidence

ORD record
ord-e86ca7d9e38543bbbfb490f8da321a12
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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