Triethylamine → HCID 59580742, compound

HRID 533335Notes

Reaction equation

HRID 533335 reaction equation
[Cl:1][C:2]1[S:3][C:4]([C:8]([OH:10])=O)=[C:5]([Cl:7])[N:6]=1.CCN(CC)CC.C1(P([N:32]=[N+:33]=[N-:34])(C2C=CC=CC=2)=O)C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[S:3][C:4]([C:8]([N:32]=[N+:33]=[N-:34])=[O:10])=[C:5]([Cl:7])[N:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 123331692,4-Dichloro-1,3-thiazole-5-carboxylic acid

Product 1

HCID 59580742HCID 59580742, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2,4-dichloro-thiazole-5-carboxylic acid (1.98 g, 10 mmol) in toluene (50 mL) was added Et3N (1.01 g, 10 mmol) followed by diphenyl phosphoryl azide (2.75 g, 10 mmol). The reaction mixture was stirred at room temperature for 20 h. The reaction mixture was concentrated in vacuo and purified by silica gel chromatography (0 to 100% ethyl acetate/hexanes) to afford product as a brown solid (1.82 g, 82%): 13C NMR (75 MHz, CDCl3) δ 163.33, 156.83, 143.94, 124.02.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by silica gel chromatography (0 to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-56c12fe2a90d4057ae13ed41371c70d6
Source dataset
uspto-grants-2014_10
Patent number
US08853246B2

Reaction notes

Loading…