Hydrochloric Acid → HCID 14478919, compound

HRID 620004Notes

Reaction equation

HRID 620004 reaction equation
[CH3:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[C:6]([NH:11][C:12](=[O:14])[CH3:13])[C:3]=1[C:4]#[N:5].Cl.[Br:16]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>O.C(Cl)(Cl)(Cl)Cl>[CH3:1][C:2]1[C:9]([CH2:10][Br:16])=[CH:8][CH:7]=[C:6]([NH:11][C:12](=[O:14])[CH3:13])[C:3]=1[C:4]#[N:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6547Azobisisobutyronitrile2×HCID 67184N-bromobutanimideHCID 144789182,3-Dimethyl-6-acetamidobenzonitrile

Product 1

HCID 14478919HCID 14478919, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

In a carefully dried Pyrex reaction vessel were combined 10 g of 2,3-dimethyl-6-acetamidobenzonitrile, 300 ml of CCl4, and 200 ml of HCl-free CHCl3 under argon. To this solution was added 10.8 g of N-bromosuccinimide (recrystallized from H2O) and 0.5 g of azo bisisobutyronitrile (AIBN). The reaction was heated to reflux and irradiated with an external General Electric sunlamp. The initially yellow reaction turned red-brown after 1 h when an additional 0.5 g of AIBN was added. After another 2 h, the reaction mixture was poured into H2O, separated, and the aqueous layer reextracted with CHCl3. The combined CHCl3 layers were washed with H2O, saturated NaHCO3 solution, and brine. The dried organic solution was evaporated at reduced pressure and the residue was crystallized from ethyl acetate to yield 6 g (42%) of the title compound, m.p. 152°-153° C. NMR (CDCl3) 2.30 (3H, s, CH3CON), 2.60 (3H, s, CH3), 4.50 (2H, s, --CH2Br), 7.40 (1H, d, ArH), 8.10 (1H, d, ArH), Anal. Calc'd for C11H11BrN2O: C, 49.5; H, 4.15; N, 10.5. Found: C, 50.3, H, 4.31; N, 10.6.

Workup

  1. customIn a carefully dried Pyrex reaction vessel
  2. temperatureThe reaction was heated
  3. temperatureto reflux
  4. customirradiated with an external General Electric sunlamp
  5. customThe initially yellow reaction
  6. waitAfter another 2 h
  7. customseparated
  8. washThe combined CHCl3 layers were washed with H2O, saturated NaHCO3 solution, and brine
  9. customThe dried organic solution was evaporated at reduced pressure
  10. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-aa6e0cd6454c4854b73e2b74a6816f25
Source dataset
uspto-grants-1989_04
Patent number
US04818753

Reaction notes

Loading…