Sodium Carbonate → HCID 58241694, compound

HRID 2367921Notes

Reaction equation

HRID 2367921 reaction equation
[CH3:1][CH:2]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH:15]([CH3:20])[CH2:16][CH:17]([CH3:19])[CH3:18])=[CH:10][CH:9]=1)[CH2:3][CH:4]([CH3:6])[CH3:5].[CH2:21]([CH:23]([CH2:26][CH2:27][CH2:28][CH3:29])[CH:24]=O)[CH3:22].[Na].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.O>[CH3:20][CH:15]([N:14]([CH2:24][CH:23]([CH2:21][CH3:22])[CH2:26][CH2:27][CH2:28][CH3:29])[C:11]1[CH:12]=[CH:13][C:8]([N:7]([CH:2]([CH3:1])[CH2:3][CH:4]([CH3:5])[CH3:6])[CH2:24][CH:23]([CH2:21][CH3:22])[CH2:26][CH2:27][CH2:28][CH3:29])=[CH:9][CH:10]=1)[CH2:16][CH:17]([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312412-EthylhexanalHCID 177737N~1~,N~4~-Bis(4-methylpentan-2-yl)benzene-1,4-diamineHCID 5360545Sodium

Product 1

HCID 58241694HCID 58241694, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

N,N′-di-(1,3-dimethylbutyl)-p-phenylenediamine (17 g, 61.5 mmol) and 2-ethylhexanal (18.53 g, 144.5 mmol) were dissolved in dichloromethane (500 mL) and were stirred together in a 1 liter round bottomed flask fitted with a condenser and magnetic stirring at room temperature whilst sodium triacetoxyhydroborate (30.63 g, 144.5 mmol) was added portionwise over 1 hour. The mixture was left standing for a total of 18 hours. The crude product was stirred with 150 ml water for a few minutes followed by addition of aqueous sodium carbonate solution (60 g in 250 ml water) in portions. Most of the effervescence subsided after 50% of this had been added. The mixture was stirred with a further 100 ml water and separated using a separating funnel. The organic phase was washed with water (500 ml+750 ml) and brine (500 ml). It was then dried with magnesium sulphate, filtered through celite 521 and evaporated to leave a dark brown oil. The product was chromatographed (eluent 5% EtOAc in heptane). Relevent fractions were combined and concentrated to afford the product as a dark oil (28.6 g, 93% yield).

Workup

  1. customfitted with a condenser
  2. additionwas added portionwise over 1 hour
  3. waitThe mixture was left
  4. customstanding for a total of 18 hours
  5. additionthis had been added
  6. customseparated
  7. washThe organic phase was washed with water (500 ml+750 ml) and brine (500 ml)
  8. dry with materialIt was then dried with magnesium sulphate
  9. filtrationfiltered through celite 521
  10. customevaporated
  11. customto leave a dark brown oil
  12. customThe product was chromatographed (eluent 5% EtOAc in heptane)
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-2c6466c984b940d4929c1e2c2d609a60
Source dataset
uspto-grants-2014_04
Patent number
US08703682B2

Reaction notes

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