Benzoyl chloride → HCID 23085720, compound

HRID 2243095Notes

Reaction equation

HRID 2243095 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:10]=1[C:11]#[N:12].[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C1C=CN=CC=1)C.ClCCl>[C:20]([NH:12][CH2:11][C:10]1[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:9]=1[NH2:8])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 285322-Amino-5-nitrobenzonitrile

Product 1

HCID 23085720HCID 23085720, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (116 ml, 0.835 mol) and DMAP (2.0 g, 0.016 mol) are added to 2-amino-5-nitrobenzonitrile (68 g, 0.33 mol) in dichloromethane (1 litre). The mixture is cooled to +5° C., and benzoyl chloride (38.8 ml, 0.33 mol) in dichloromethane (50 ml) is added. The resulting mixture is stirred for 2 hours and then concentrated. The residue is taken up in 10/1 water/ethanol (550 ml) and the product is filtered off and recrystallized from isopropyl ether. Yield: 88.5 g (97%); IR (KBr): 3375, 3213, 1638, 1547, 1319 cm−1; 1H-NMR (d6-DMSO) 8.15 (m, 1H); 7.85 (m, 4H); 7.51 (m, 4H); 6.68 (m, 3H); 4.30 (m, 2H).

Workup

  1. temperatureThe mixture is cooled to +5° C.
  2. concentrationconcentrated
  3. filtrationthe product is filtered off
  4. customrecrystallized from isopropyl ether

Sources & evidence

ORD record
ord-223387b6ed3c421a96d83af4dab58e52
Source dataset
uspto-grants-2010_03
Patent number
US07674809B2

Reaction notes

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