Aspirin → Acetic acid 2-[4-methyl-5-(2-nitrooxy-ethyl)-thiazol-2-ylcarbamoyl]-phenyl ester

HRID 457888Notes

Reaction equation

HRID 457888 reaction equation
[C:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=O)(=[O:3])[CH3:2].[CH3:14][C:15]1[N:16]=[C:17]([NH2:26])[S:18][C:19]=1[CH2:20][CH2:21][O:22][N+:23]([O-:25])=[O:24]>>[CH3:14][C:15]1[N:16]=[C:17]([NH:26][C:7]([C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[O:4][C:1](=[O:3])[CH3:2])=[O:9])[S:18][C:19]=1[CH2:20][CH2:21][O:22][N+:23]([O-:25])=[O:24]

Participants

3

Reactant 2

HCID 2244AspirinHCID 115574994-Methyl-5-(2-nitrooxy-ethyl)-thiazol-2-ylamine

Product 1

HCID 58820306Acetic acid 2-[4-methyl-5-(2-nitrooxy-ethyl)-thiazol-2-ylcarbamoyl]-phenyl esterYield 25%

Procedure

Pet-159 was prepared according to the general procedure described hereinabove and the procedure described above for the preparation of Pet-154, using 2-acetoxy-benzoic acid (Aspirin) and 4-methyl-5-(2-nitrooxy-ethyl)-thiazol-2-ylamine (Pet-10) as the starting materials, in an overall yield of 25%.

Workup

  1. customPet-159 was prepared
  2. customthe procedure described above for the preparation of Pet-154

Sources & evidence

ORD record
ord-c40e9dcba1354645905701eb1f321e55
Source dataset
uspto-grants-2007_03
Patent number
US07189750B2

Reaction notes

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