Acetonitrile → HCID 71076878, compound

HRID 923582Notes

Reaction equation

HRID 923582 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)=O.[Br:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[CH:16][CH:15]=1.C(#N)C>CN1C(=O)CCC1>[Br:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]2[O:19][CH:2]=[C:3]([C:5]3[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=3)[N:20]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 696834-BromobenzamideHCID 986544-(Bromoacetyl)benzonitrile

Product 1

HCID 71076878HCID 71076878, compoundYield 17.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
135 °C

Procedure

To a stirring solution of 4-(2-bromoacetyl)benzonitrile (7.13 g, 31.8 mmol) in NMP (15 mL) was added 4-bromobenzamide (5.31 g, 26.5 mmol) and the reaction mixture heated to 135° C. for 18 h. The reaction mixture was allowed to cool to room temperature then treated with acetonitrile (25 mL) and stirred for 3 h. The precipitate was collected by filtration and washed with acetonitrile (2×5 mL) to afford 1.51 g (17%) of 4-(2-(4-bromophenyl)oxazol-4-yl)benzonitrile INT-42 as a light brown powder. LCMS-ESI (m/z) calculated for C16H9BrN2O: 324; found 325 [M+H]+, tR=2.86 min (Method 10). 1H NMR (400 MHz, DMSO) δ 8.94 (s, 1H), 8.03 (d, J=8.2 Hz, 2H), 7.98-7.91 (m, 4H), 7.76 (d, J=8.5 Hz, 2H).

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with acetonitrile (2×5 mL)

Sources & evidence

ORD record
ord-c054ed3c919240a68f483df98ccc459e
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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