2-Bromo-2'-nitroacetophenone → 6-[4-(2-Nitro-phenyl)-oxazol-2-yl]-hexanoic acid ethyl ester

HRID 1616624Notes

Reaction equation

HRID 1616624 reaction equation
CO[C:3](=O)[CH2:4][CH2:5][CH2:6][C:7]1[O:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-:20])=[O:19])[N:11]=1.BrCC(C1C=CC=CC=1[N+]([O-])=O)=O.[CH2:35]([O:37][C:38](=[O:47])[CH2:39]CCCCC(=O)N)[CH3:36]>>[CH2:35]([O:37][C:38](=[O:47])[CH2:39][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[O:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-:20])=[O:19])[N:11]=1)[CH3:36]

Participants

4

Reactant 3

HCID 2440252-Bromo-2'-nitroacetophenoneHCID 542980746-Carbamoyl-hexanoic acid ethyl esterHCID 591677914-[4-(2-Nitro-phenyl)-oxazol-2-yl]-butyric acid methyl ester

Product 1

HCID 591677726-[4-(2-Nitro-phenyl)-oxazol-2-yl]-hexanoic acid ethyl esterYield 26%

Procedure

Using a method similar to the procedure described for the preparation of 4-[4-(2-nitro-phenyl)-oxazol-2-yl]-butyric acid methyl ester; reaction of 2-bromo-2′-nitroacetophenone (8.9 g, 36.5 mmol) with 6-carbamoyl-hexanoic acid ethyl ester (9.1 g, 48.7 mmol) gives 6-[4-(2-nitro-phenyl)-oxazol-2-yl]-hexanoic acid ethyl ester (3.19 g, 26%). MS (ES): (M+1)+ 333.2, 334.4 m/z.

Sources & evidence

ORD record
ord-b3093959c6564d86bef14a60d6532498
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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