Hexylamine → HCID 24830401, compound

HRID 2410048Notes

Reaction equation

HRID 2410048 reaction equation
[CH2:1]([N:7]=[C:8]=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:10]([NH2:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[C:17](Cl)(=[O:22])[CH2:18][C:19](Cl)=[O:20].C(N(C(C)C)CC)(C)C.[N:33]([CH2:36][C:37]([O:39]CC)=[O:38])=[C:34]=[O:35]>ClCCl>[CH2:1]([N:7]1[C:19]([OH:20])=[C:18]([C:34]([NH:33][CH2:36][C:37]([OH:39])=[O:38])=[O:35])[C:17](=[O:22])[N:16]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:8]1=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 5

HCID 8102HexylamineHCID 74269Propanedioyl dichlorideHCID 75659Hexyl isocyanateHCID 76283Ethyl isocyanatoacetateHCID 81531Diisopropylethylamine

Product 1

HCID 24830401HCID 24830401, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Hexyl isocyanate (728 uL, 5.0 mmoles) was added to a solution of n-hexylamine (660 uL, 5.0 mmoles) in dichloromethane (100 mL) and the mixture stirred for 1 hour. Malonyl dichloride (486 uL, 5.0 mmoles) was added and the mixture was heated to gentle reflux for 1 hour. The mixture was washed with 1 molar hydrochloric acid (×2), dried and evaporated. The residue was redissolved in dichloromethane (50 mL) and diisopropylethylamine (1.73 mL, 10 mmoles) and the mixture was treated with ethyl isocyanatoacetate (561 uL, 5.0 mmoles). After stirring overnight the mixture was washed with 1 molar hydrochloric acid, dried and evaporated. The residue was dissolved in ethanol (5 mL) and treated with 6 molar sodium hydroxide (2.0 mL). The mixture was stirred for 1 hour, acidified and extracted into ethyl acetate. The organic solution was washed with 1 molar hydrochloric acid, dried and evaporated. The crude product was slurried in hexane to afford the title compound (890 mg, 45%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.10 (br. s, 1 H), 10.10 (t, J=4.80 Hz, 1 H), 4.13 (d, J=5.81 Hz, 2 H), 3.75-3.84 (m, 4 H), 1.53 (s, 4 H), 1.26 (s, 12 H), 0.82-0.90 (m, 6 H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto gentle reflux for 1 hour
  3. washThe mixture was washed with 1 molar hydrochloric acid (×2)
  4. customdried
  5. customevaporated
  6. dissolutionThe residue was redissolved in dichloromethane (50 mL)
  7. stirringAfter stirring overnight the mixture
  8. washwas washed with 1 molar hydrochloric acid
  9. customdried
  10. customevaporated
  11. dissolutionThe residue was dissolved in ethanol (5 mL)
  12. additiontreated with 6 molar sodium hydroxide (2.0 mL)
  13. stirringThe mixture was stirred for 1 hour
  14. extractionextracted into ethyl acetate
  15. washThe organic solution was washed with 1 molar hydrochloric acid
  16. customdried
  17. customevaporated

Sources & evidence

ORD record
ord-646faacada544b6e91c4aaa0e9216e0c
Source dataset
uspto-grants-2014_08
Patent number
US08815884B2

Reaction notes

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