Butyl nitrite → HCID 86587986, compound

HRID 1828175Notes

Reaction equation

HRID 1828175 reaction equation
[O-]CC.[Na+].[CH:5]1([N:10]2[C:14]3[CH:15]=[CH:16][C:17]([C:19](=[O:28])[CH2:20][C:21]4[CH:22]=[C:23]([CH3:27])[CH:24]=[CH:25][CH:26]=4)=[CH:18][C:13]=3[N:12]([CH3:29])[C:11]2=[O:30])[CH2:9][CH2:8][CH2:7][CH2:6]1.[N:31](OCCCC)=[O:32]>C(O)C.O>[CH:5]1([N:10]2[C:14]3[CH:15]=[CH:16][C:17]([C:19](=[O:28])[C:20]([C:21]4[CH:22]=[C:23]([CH3:27])[CH:24]=[CH:25][CH:26]=4)=[N:31][OH:32])=[CH:18][C:13]=3[N:12]([CH3:29])[C:11]2=[O:30])[CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 10996Butyl nitriteHCID 2723922Sodium ethoxideHCID 23581457HCID 23581457, compound

Product 1

HCID 86587986HCID 86587986, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Sodium ethoxide (9.27 mL of a 21% solution in ethanol, 28.6 mmol) was added to ethanol (12 mL) at 0 deg C. After 5 minutes, 1-cyclopentyl-3-methyl-5-m-tolylacetyl-1,3-dihydro-benzoimidazol-2-one (prepared as described in the general procedure, 5 gm, 14.3 mmol) was added. n-Butyl nitrite (3.34 mL, 28.6 mmol) was then added dropwise over 5 minutes. When the addition was complete, the flask was covered with a septum and allowed to stand in the refrigerator overnight, after which time LCMS of an aliquot showed essentially complete reaction. The reaction mixture was diluted with 300 mL of water and allowed to stir at room temperature overnight. The resulting precipitate was filtered and dried in vacuo. The yellow solid was slurried with benzene for 2 hours and filtered to afford 4.0 gm of a pale tan solid. The title oxime is formed a ca. 10:1 mixture of isomers.

Workup

  1. additionwas added
  2. additionWhen the addition
  3. customto stand in the refrigerator overnight
  4. customreaction
  5. filtrationThe resulting precipitate was filtered
  6. customdried in vacuo
  7. waitThe yellow solid was slurried with benzene for 2 hours
  8. filtrationfiltered

Sources & evidence

ORD record
ord-8580c422b2b04155b15c58dac3b2921d
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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