Triethylamine → HCID 59580742, compound

HRID 1470442Notes

Reaction equation

HRID 1470442 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-8c4d738e886a4f389ec8fa84e848ab97
Source dataset
uspto-grants-2015_04
Patent number
US09006446B2

Reaction notes

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