Sodium hydride → HCID 86741420, compound

HRID 1608007Notes

Reaction equation

HRID 1608007 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][NH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[H-].[Na+].Br[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]([CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:29](=[O:34])[C:30]([F:33])([F:32])[F:31]>CN(C)C=O>[NH2:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][N:12]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]([CH2:35][CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:29](=[O:34])[C:30]([F:33])([F:32])[F:31])[C:13](=[O:18])[C:14]([F:15])([F:16])[F:17])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 12807541N-[2-(3-Amino-4-methoxyphenyl)ethyl]-2,2,2-trifluoroacetamideHCID 19850148HCID 19850148, compound

Product 1

HCID 86741420HCID 86741420, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N-[2-(3-Amino-4-methoxyphenyl)ethyl]-2,2,2-trifluoro acetamide (2.62 g., 0.01 moles) in dry dimethylformamide (50 ml) was added dropwise with stirring to sodium hydride (0.3 g., 80% oil dispersion, 0.01 moles) in dry dimethylformamide (50 ml) under nitrogen. The solution was warmed at 60° for 30 min then cooled and N-(6-bromohexyl)-2,2,2-trifluoro-N-(2-phenylethyl)acetamide (3.80 g., 0.01 mole) was added. The solution was stirred for 4 hours then quenched with water and extracted with ethyl acetate. The extracts were washed with water dried and evaporated to give crude N-[2-(3-amino-4-methoxyphenyl)ethyl]-N'-(2-phenylethyl)-1,6-hexanediylbis (2,2,2-trifluoroacetamide) (3.1 g) as a pale brown oil.

Workup

  1. temperatureThe solution was warmed at 60° for 30 min
  2. temperaturethen cooled
  3. customthen quenched with water
  4. extractionextracted with ethyl acetate
  5. washThe extracts were washed with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-ad28860f5773428a83b4f797c7f71ae9
Source dataset
uspto-grants-1989_09
Patent number
US04868306

Reaction notes

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