Ammonium Chloride → HCID 57801035, compound

HRID 1817676Notes

Reaction equation

HRID 1817676 reaction equation
CON(C)[C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)=[O:5].[NH4+].[Cl-]>O1CCCC1>[C:9]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=[CH:11][C:6]([C:4](=[O:5])[CH2:10][CH2:11][CH2:6][CH:7]=[CH2:8])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 10060247N-Methoxy-N-methyl-4-phenylbenzamide

Product 1

HCID 57801035HCID 57801035, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Bromo-1-pentene (1.5 g) was gently heated with magnesium turnings (1 g) in anhydrous tetrahydrofuran (15 ml) until reaction started. The mixture was left to reflux without further heating to give the Grignard reagent, then allowed to cool to room temperature. Biphenyl-4-carboxylic acid methoxy-methyl amide (4 g) was dissolved in anhydrous tetrahydrofuran (20 ml) and chilled in an ice bath. The Grignard reagent was added dropwise with vigorous stirring. Following addition, the mixture was allowed to warm to room temperature and stirring continued for 2 hours. Saturated NH4Cl solution (50 ml) was added and the mixture extracted with petrol. Drying with Na2SO4 followed by evaporation gave an oil. Column chromatography (petrol:ethyl acetate 5:1) gave the title compound as a white solid (70%). δC (CDCl3, 62.9 MHz): 23.4, 33.3, 37.8, 115.4, 127.3, 127.3, 128.2, 128.7, 129.0, 135.8, 138.1, 139.9, 145.6 and 199.9. δH (CDCl3, 250 MHz): 1.88 (2H, quintet, J 7.32), 2.17 (2H, quintet, J 7.32), 3.00 (2H, t, J 7.32), 5.03 (2H, m), 5.84 (1H, m), 7.62 (2H, d, J 7.9), 7.47 (3H, m), 7.67 (2H, d, J 7.9) and 8.03 (2H, d, J 7.9).

Workup

  1. temperaturechilled in an ice bath
  2. additionaddition
  3. temperatureto warm to room temperature
  4. extractionthe mixture extracted with petrol
  5. dry with materialDrying with Na2SO4
  6. customfollowed by evaporation
  7. customgave an oil

Sources & evidence

ORD record
ord-e7c8389f92f5441bb0f5479a56f1dd32
Source dataset
uspto-grants-2009_10
Patent number
US07598289B2

Reaction notes

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