Benzoyl isocyanate → HCID 10342808, compound

HRID 1672343Notes

Reaction equation

HRID 1672343 reaction equation
[C:1]([N:9]=[C:10]=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:22]=[CH:21][C:20]2[N+:19]([O-])=C[C:17]3[N:24]=[CH:25][N:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[Cl:33])[C:16]=3[C:15]=2[CH:14]=1>C(Cl)Cl>[Cl:12][C:13]1[CH:22]=[CH:21][C:20]2[N:19]=[C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:17]3[N:24]=[CH:25][N:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[Cl:33])[C:16]=3[C:15]=2[CH:14]=1

Participants

4

Reactant 2

HCID 78210Benzoyl isocyanateHCID 10359250HCID 10359250, compound

Product 1

HCID 10342808HCID 10342808, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.644 g (3.939 mmol) benzoyl isocyanate in 10 ml CH2Cl2 is added within 10 min to 1 g (3.029 mmol) of 8-chloro-1-(2-chloro-phenyl)-1H-imidazo[4,5-c]quinoline 5-oxide (Example 71) in 10 ml CH2Cl2. The reaction mixture is heated and kept under reflux for 7 h. The solvent is evaporated, and the residue is purified by chromatography (CH2Cl2-methanol 97.5:2.5). The compound is crystallized from ethyl acetate-hexane. mp: 255-258° C.; MS: 433 (M++1); HPLC: tret=10.91 min (Grad 1).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 7 h
  3. customThe solvent is evaporated
  4. customthe residue is purified by chromatography (CH2Cl2-methanol 97.5:2.5)
  5. customThe compound is crystallized from ethyl acetate-hexane
  6. customtret=10.91 min (Grad 1)

Sources & evidence

ORD record
ord-a5cf71cc666342e882b27c040e7151a4
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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