Dimethylformamide → HCID 2557920, compound

HRID 1361012Notes

Reaction equation

HRID 1361012 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=O.CN(C)C=O.S(Cl)(Cl)=O.[NH2:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[C:27]#[N:28]>ClCCl.O.C(N(CC)CC)C>[C:27]([C:26]1[CH:25]=[C:24]([NH:23][C:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[O:13])[CH:31]=[CH:30][CH:29]=1)#[N:28]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 71232-Naphthoic acidHCID 167023-AminobenzonitrileHCID 24386Thionyl Chloride

Product 1

HCID 2557920HCID 2557920, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

2-Naphtoic acid (10 g, 58 mmol) was dissolved in dichloromethane (100 mL) and N,N-dimethylformamide (0.2 mL) was added followed by thionyl chloride (5.1 ml, 70 mmol). The mixture was heated at reflux temperature for 2 hours. After cooling to room temperature, the mixture was added dropwise to a mixture of 3-aminobenzonitril (6.90 g, 58 mmol) and triethyl amine (10 mL) in dichloromethane (75 mL). The resulting mixture was stirred at room temperature for 30 minutes. Water (50 mL) was added and the volatiles was exaporated in vacuo. The resulting mixture was filtered and the filter cake was washed with water followed by heptane (2×25 mL). Drying in vacuo at 50° C. for 16 hours afforded 15.0 g (95%) of N-(3-cyanophenyl)-2-naphtoic acid amide.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 2 hours
  3. filtrationThe resulting mixture was filtered
  4. washthe filter cake was washed with water
  5. customDrying in vacuo at 50° C. for 16 hours

Sources & evidence

ORD record
ord-2c4e44e126794d829a6eb6b46244d98c
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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