Nitrogen → 2-[4-(2-Methyl-[1,3]dioxolan-2-yl)-butyl]-oxazole-4-carbonyl chloride

HRID 1189362Notes

Reaction equation

HRID 1189362 reaction equation
N#N.[CH3:3][C:4]1([CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[O:14][CH:15]=[C:16]([C:18]([OH:20])=O)[N:17]=2)[O:8][CH2:7][CH2:6][O:5]1.CN(C=O)C.C(Cl)(=O)C([Cl:29])=O>C1(C)C=CC=CC=1>[CH3:3][C:4]1([CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[O:14][CH:15]=[C:16]([C:18]([Cl:29])=[O:20])[N:17]=2)[O:8][CH2:7][CH2:6][O:5]1

Participants

6

Reactant 4

HCID 947NitrogenHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 671284612-[4-(2-Methyl-[1,3]dioxolan-2-yl)-butyl]-oxazole-4-carboxylic acid

Product 1

HCID 866649012-[4-(2-Methyl-[1,3]dioxolan-2-yl)-butyl]-oxazole-4-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a suspension of 2-[4-(2-methyl-[1,3]dioxolan-2-yl)-butyl]-oxazole-4-carboxylic acid (489 mg, 1.92 mmol) in toluene (20 mL) was treated with a drop of DMF followed by oxalyl chloride (0.20 mL, 2.30 mmol) and the resulting yellow solution was stirred at rt for 1 h. The solvent was then removed under reduced pressure (coevaporation with toluene) to give 2-[4-(2-methyl-[1,3]dioxolan-2-yl)-butyl]-oxazole-4-carbonyl chloride as a yellow oil. LC-MS-conditions 02: tR=0.96 min [M+H]+=274.37.

Workup

  1. customThe solvent was then removed under reduced pressure (coevaporation with toluene)

Sources & evidence

ORD record
ord-b0b7819dfce74e0db206c8883b96711c
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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