Acetic Acid → N-Ethyl-N'-[6-(5-methyl-1,2,4-oxadiazol-3-yl)-1,3-benzothiazol-2-yl]urea

HRID 9173Notes

Reaction equation

HRID 9173 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[CH:15]=[C:14]([C:16](=[N:18][OH:19])[NH2:17])[CH:13]=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].[C:20](O)(=O)[CH3:21]>>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[CH:15]=[C:14]([C:16]3[N:17]=[C:20]([CH3:21])[O:19][N:18]=3)[CH:13]=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 865889792-[(Ethylamino)carbonyl]amino-1,3-benzothiazole-6-carboxamideoxime

Product 1

HCID 21985589N-Ethyl-N'-[6-(5-methyl-1,2,4-oxadiazol-3-yl)-1,3-benzothiazol-2-yl]urea

Conditions

Temperature
110 °C

Procedure

About 50 mg of 2-[(ethylamino)Carbonyl]amino-1,3-benzothiazole-6-carboxamideoxime was charged into about 1 mL of glacial acetic acid. The mixture was heated to about 110° C. then stirred at this temperature for about 12–20 hours. The solution was cooled to room temperature and the solvent was removed under reduced pressure. The residue was then further purified by preparative HPLC. 1H NMR 1.10 (t, 3H), 2.67 (s, 3H), 3.17 (m, 2H), 6.74 (s, 1H), 7.73 (d, 1H), 7.97 (d, 1H), 8.53 (s, 1H), 10.9 (s, 1H); LC/MS 2.69 min, 304 (M+1), 302 (M−1).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was then further purified by preparative HPLC
  4. customLC/MS 2.69 min, 304 (M+1), 302 (M−1)

Sources & evidence

ORD record
ord-e7c3ed99e5624aeda2d8f375a0cf6650
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Reaction notes

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