Acetonitrile → HCID 11532042, compound

HRID 2112232Notes

Reaction equation

HRID 2112232 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].N([O-])=O.[Na+].[CH3:15][C:16]1([CH3:35])[CH:20]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)[C:19]2[C:28]([CH3:34])=[CH:29][C:30]([CH3:33])=[C:31]([CH3:32])[C:18]=2[O:17]1.C(#[N:38])C>Cl.O>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([N:8]=[N:38][C:29]2[C:30]([CH3:33])=[C:31]([CH3:32])[C:18]3[O:17][C:16]([CH3:35])([CH3:15])[CH:20]([C:21]4[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=4)[C:19]=3[C:28]=2[CH3:34])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 74754-NitroanilineHCID 10850374Benzofuran, 2,3-dihydro-2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-HCID 23668193Sodium Nitrite

Product 1

HCID 11532042HCID 11532042, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

4-Nitroaniline (10.4 g) was dissolved in 2N hydrochloric acid (150 mL) by heating, and then cooled to 0 to 5° C. To the solution was added a solution of sodium nitrite (5.2 g) in water (15 mL), and the mixture was stirred for 15 minutes. To the mixture were added 2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran (14.0 g) and acetonitrile (150 mL). The reaction mixture was stirred at 65 to 70° C. for one hour under a nitrogen atmosphere, and then allowed to cool to room temperature. Precipitated crystals were collected by filtration, and washed with 1N hydrochloric acid and water. The crystals were dried under reduced pressure to obtain the title compound as a brown solid (21.0 g, yield 100%).

Workup

  1. temperatureby heating
  2. stirringThe reaction mixture was stirred at 65 to 70° C. for one hour under a nitrogen atmosphere
  3. temperatureto cool to room temperature
  4. customPrecipitated crystals
  5. filtrationwere collected by filtration
  6. washwashed with 1N hydrochloric acid and water
  7. customThe crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-c4f511eedaf54ed4809c3c9e2112c3e4
Source dataset
uspto-grants-2009_04
Patent number
US07521545B2

Reaction notes

Loading…