4-Chlorobenzaldehyde → HCID 54886778, compound

HRID 521372Notes

Reaction equation

HRID 521372 reaction equation
[Si]([C:5]#[N:6])(C)(C)C.[Cl:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1.[Br:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1>CO.S(=O)(=O)(O)N>[Br:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][CH:12]([C:11]2[CH:14]=[CH:15][C:8]([Cl:7])=[CH:9][CH:10]=2)[C:5]#[N:6])=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 78074-BromoanilineHCID 82115Trimethylsilyl cyanide

Product 1

HCID 54886778HCID 54886778, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 5987Sulfamic AcidCatalystHCID 887MethanolSolvent

Procedure

TMSCN (19.9 mL, 149 mmol) was added to a solution of 4-chlorobenzaldehyde (20.0 g, 142 mmol), 4-bromoaniline (25.1 g, 146 mmol), and sulfamic acid (0.691 g, 7.11 mmol) in MeOH (56.9 mL), and the reaction mixture was stirred at room temperature for 6 hours. The reaction mixture was filtered, and the filter cake was washed with ethanol, affording 2-(4-bromophenylamino)-2-(4-chlorophenyl)acetonitrile as a solid (38.0 g, 83%). 1H NMR (400 MHz, d6-DMSO) δ □7.53 (d, J=8.2 Hz, 2H), 7.44 (d, J=8.6 Hz, 2H), 7.37 (d, J=9.0 Hz, 2H), 6.64 (d, J=9.0 Hz, 2H), 5.38 (d, J=9.0 Hz, 1H), 4.06 (d, J=9.0 Hz, 1H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe filter cake was washed with ethanol

Sources & evidence

ORD record
ord-e969da852c0849e197259f72b22ef6c6
Source dataset
uspto-grants-2016_05
Patent number
US09328091B2

Reaction notes

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