Ammonia → HCID 18783143, compound

HRID 1420873Notes

Reaction equation

HRID 1420873 reaction equation
[CH3:1][C:2]1(O)[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4]([CH3:11])([CH3:10])[CH2:3]1.[OH2:13].N.[C:15](#[N:17])[CH3:16]>>[C:15]([NH:17][C:2]1([CH3:1])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4]([CH3:11])([CH3:10])[CH2:3]1)(=[O:13])[CH3:16]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 6342AcetonitrileHCID 1422881,3,3,5,5-Pentamethylcyclohexanol

Product 1

HCID 18783143HCID 18783143, compoundYield 60%

Conditions

Temperature
-50 °C

Procedure

To a vigorously stirred solution of 1,3,3,5,5-pentamethylcyclohexanol (3-13) (3.0 g, 17.65 mmol) in acetonitrile (20 ml) fuming HNO3 (6ml) was added dropwise, keeping temperature below 45° C. The resulting mixture was stirred at -50° C. for 6 h, then it was cooled, poured into water (30 ml) ana neutralised with aqueous NH3. Aqueous phase was extracted with ether (3*30 ml). The combined ether phases were washed with saline (30 ml), then dried over MgSO4, filtered and evaporated. The crude product was crystallised from cold acetonitrile to give 223 g (60%) of 14-2 as a white crystals, m.p. 110° C.

Workup

  1. customtemperature below 45° C
  2. temperatureit was cooled
  3. extractionAqueous phase was extracted with ether (3*30 ml)
  4. washThe combined ether phases were washed with saline (30 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was crystallised from cold acetonitrile

Sources & evidence

ORD record
ord-11ed142ceef94d2e99b3f55577bf2078
Source dataset
uspto-grants-2000_06
Patent number
US06071966

Reaction notes

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