Toluene → HCID 136133797, compound

HRID 973975Notes

Reaction equation

HRID 973975 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[N:13]=[C:14]=[O:15])([CH3:3])[CH3:2].C[Si]([N:20]=[N+:21]=[N-:22])(C)C.C1(C)C=CC=CC=1>O>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:11])[CH3:12])[C:5]=1[N:13]1[C:14](=[O:15])[NH:22][N:21]=[N:20]1)([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 1140TolueneHCID 78378AzidotrimethylsilaneHCID 922592,6-Diisopropylphenyl isocyanate

Product 1

HCID 136133797HCID 136133797, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

37.1 g of 2,6-diisopropylphenyl isocyanate and 50 ml of trimethylsilyl azide are stirred for 24 hours at +140° C. The mixture is then cooled to room temperature and stirred with 250 ml of toluene and with 250 ml of water. After 1 hour, the phases are separated and the aqueous phase is extracted with toluene. The combined organic phases are extracted four times with 250 ml of 15% sodium hydroxide solution each time, and then the aqueous phases are combined and washed with ether. After acidification with semi-concentrated hydrochloric acid, crude 1-(2,6-diisopropylphenyl)-5-oxo-2-tetrazoline precipitates. This is recrystallised from a mixture of hexane and toluene in a ratio of 10:1. Melting point 177°-178.5°.

Workup

  1. customthe phases are separated
  2. extractionthe aqueous phase is extracted with toluene
  3. extractionThe combined organic phases are extracted four times with 250 ml of 15% sodium hydroxide solution each time
  4. washwashed with ether
  5. customAfter acidification with semi-concentrated hydrochloric acid, crude 1-(2,6-diisopropylphenyl)-5-oxo-2-tetrazoline precipitates
  6. customThis is recrystallised from a mixture of hexane and toluene in a ratio of 10:1

Sources & evidence

ORD record
ord-f67432935cbe4283901185dd81b856f1
Source dataset
uspto-grants-1991_11
Patent number
US05066667

Reaction notes

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