Water → HCID 15346053, compound

HRID 374962Notes

Reaction equation

HRID 374962 reaction equation
[CH2:1]([C:3]([O:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:9]=1[C:10]([NH2:12])=[O:11])([CH2:5][CH3:6])[CH3:4])[CH3:2].[CH3:18][CH2:19][CH2:20]Br.O>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+].C1(C)C=CC=CC=1>[CH2:18]([NH:12][C:10](=[O:11])[C:9]1[C:13]([Cl:17])=[CH:14][CH:15]=[CH:16][C:8]=1[O:7][C:3]([CH2:5][CH3:6])([CH2:1][CH3:2])[CH3:4])[CH2:19][CH3:20]

Participants

7

Reactant 3

HCID 962WaterHCID 78401-BromopropaneHCID 15346052HCID 15346052, compound

Product 1

HCID 15346053HCID 15346053, compoundYield 67.2%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent2×HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-[(1,1-diethylethyl)oxy]-6-chlorobenzamide (1.00 g, 3.9 mmol) and tetrabutylammonium bisulfate (0.13 g, 0.4 mmol) in 50% aqueous sodium hydroxide (25 mL) and toluene (15 mL) was heated to 100° C. and n-propyl bromide (0.43 mL, 4.7 mmol) in toluene (10 mL) was added over 30 min. The reaction was heated for 1 h, was cooled and poured into water. The mixture was extracted with ether and the organic layers were washed with brine, dried (MgSO4) and concentrated to a white solid. The crude product was purified by radial chromatography to afford 0.78 g (67%) of N-propyl 2-[(1,1-diethylethyl)oxy]-6-chlorobenzamide as a white solid: mp 100°-102° C.

Workup

  1. temperatureThe reaction was heated for 1 h
  2. temperaturewas cooled
  3. extractionThe mixture was extracted with ether
  4. washthe organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated to a white solid
  7. customThe crude product was purified by radial chromatography

Sources & evidence

ORD record
ord-c876f758466c42739f9b1a6254d1947f
Source dataset
uspto-grants-1996_01
Patent number
US05482974

Reaction notes

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