3-Isocyanatobenzonitrile → HCID 57842652, compound

HRID 735600Notes

Reaction equation

HRID 735600 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][CH3:11])=[C:4]([CH2:12][CH3:13])[CH:3]=1.[N:14]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[C:20]#[N:21])=[C:15]=[O:16]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH3:11])[C:15]([NH:14][C:17]2[CH:24]=[CH:23][CH:22]=[C:19]([C:20]#[N:21])[CH:18]=2)=[O:16])=[C:4]([CH2:12][CH3:13])[CH:3]=1

Participants

4

Reactant 2

HCID 27333153-IsocyanatobenzonitrileHCID 57842797HCID 57842797, compound

Product 1

HCID 57842652HCID 57842652, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 36C (250 mg, 1.03 mmol) and 3-isocyanatobenzonitrile (164 mg, 1.03 mg) in CH2Cl2 (10 mL) was refluxed for 30 min. The solution was concentrated in vacuo and purified by flash chromatography (0% to 100% EtOAc in hexanes) to afford 36D (250 mg, 63%) as a yellow solid. MS (ESI) m/z 386.04/388.05 (M+H)+.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. custompurified by flash chromatography (0% to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-60cf76a558694e79a8903e2a178b4d3e
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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