Benzene → HCID 45788714, compound

HRID 1628209Notes

Reaction equation

HRID 1628209 reaction equation
[C:1]([CH2:3][NH:4][C:5](=O)[C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)#[N:2].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:14].C1C=CC=CC=1>>[N:9]1[CH:10]=[CH:11][C:6]([C:5]2[S:14][C:1]([NH2:2])=[CH:3][N:4]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 14817Phosphorus sulfide (P2S5)HCID 21275762HCID 21275762, compound

Product 1

HCID 45788714HCID 45788714, compoundYield 100.5%

Procedure

A mixture of N-(cyanomethyl)isonicotinamide (0.665 g, 4.1 mmol) and phosphorus pentasulfide (1.8 g, 8.3 mmol) in benzene (5.00 ml, 56 mmol) was allowed to refluxed for 24 hours. The mixture was concentrated and the residue was purified by CombiFlash using 0-10% methanol/DCM to give 730 mg of 2-(pyridin-4-yl)thiazol-5-amine 5.3C. 400 MHz 1H NMR (CD3OD) δ: 8.51 (d, J=8.0 Hz, 2H), 7.72 (d, J=8.0 Hz, 2H), 7.07 (s, 1H). LCMS (ES+) m/z 178.

Workup

  1. temperatureto refluxed for 24 hours
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by CombiFlash

Sources & evidence

ORD record
ord-08a1e26a58994ea78a70b78ff60078d1
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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