Sodium Cyanide → 2-Amino-3-phenyl-5,7-di-tert-butyl-benzofurane

HRID 1356560Notes

Reaction equation

HRID 1356560 reaction equation
[C-:1]#[N:2].[Na+].[C:4]([C:8]1[CH:13]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:11]=[C:10]([CH:18](N(C)C)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]=1[OH:28])([CH3:7])([CH3:6])[CH3:5].C(OC)(C)(C)C>O.S1(CCCC1)(=O)=O>[NH2:2][C:1]1[O:28][C:9]2[C:8]([C:4]([CH3:6])([CH3:5])[CH3:7])=[CH:13][C:12]([C:14]([CH3:16])([CH3:15])[CH3:17])=[CH:11][C:10]=2[C:18]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 15413tert-Butyl methyl etherHCID 111519612,4-Di-tert-butyl-6-(dimethylaminophenyl-methyl)-phenol

Product 1

HCID 113930882-Amino-3-phenyl-5,7-di-tert-butyl-benzofuraneYield 99.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31347SulfolaneSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 0.98 g (20,0 mmol) of sodium cyanide in 2.0 ml of water is added to a solution of 3.39 g (10,0 mmol) of 2,4-di-tert-butyl-6-(dimethylaminophenyl-methyl)-phenol [compound (201), Table 2, prepared according to Example 2a in WO-A-99/67232] in 10 ml of sulfolane. The reaction mixture is then maintained at 120° C. for one hour. After cooling to room temperature, the reaction mixture is poured into 80 ml tert-butyl-methylether and washed three times with water. The organic phases are combined, dried over sodium sulfate and concentrated using a vacuum rotary evaporator. The residue yields 3.20 g (99%) of 2-amino-3-phenyl-5,7-di-tert-butyl-benzofurane (compound (301), Table 3), m.p. 174-178° C.

Workup

  1. customprepared
  2. temperatureAfter cooling to room temperature
  3. washwashed three times with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customa vacuum rotary evaporator

Sources & evidence

ORD record
ord-9e414ad9970442b5ae00e870855ba388
Source dataset
uspto-grants-2003_07
Patent number
US06586606B2

Reaction notes

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