Water → 2-{4-[(3,7-dimethyl-2,6-octadienyl)oxy]phenyl}-N-(3thioxo-3H-1,2,4-dithiazol-5-yl)acetoamide

HRID 1393850Notes

Reaction equation

HRID 1393850 reaction equation
[CH3:1][C:2]([CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])=[CH:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13](O)=[O:14])=[CH:8][CH:7]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:34][C:35]1[S:36][S:37][C:38](=[S:40])[N:39]=1.O>O1CCCC1>[CH3:1][C:2]([CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])=[CH:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([NH:34][C:35]2[S:36][S:37][C:38](=[S:40])[N:39]=2)=[O:14])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 2735329Xanthane hydrideHCID 545318442-{4-[(3,7-Dimethyl-2,6-octadienyl)oxy]phenyl}acetic acid

Product 1

HCID 723564392-{4-[(3,7-dimethyl-2,6-octadienyl)oxy]phenyl}-N-(3thioxo-3H-1,2,4-dithiazol-5-yl)acetoamideYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-{4-[(3,7-Dimethyl-2,6-octadienyl)oxy]phenyl}acetic acid (1.00 g,3.47 mmol) was dissolved in tetrahydrofuran (12 ml), and 1,1′-carbonyldiimidazole (0.68 g, 4.16 mmol) was added thereto. The mixture was stirred for 1 hour at room temperature, and then 3-amino-1,2,4-dithiazole-5-thione (0.42 g, 2.70 mmol) was added thereto. After being stirred for 3 hours at room temperature, the mixture, with water added thereto, was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over MgSO4, and then concentrated. The obtained residue was purified by silica gel chromatography (chloroform), to give 2-{4-[(3,7-dimethyl-2,6-octadienyl)oxy]phenyl}-N-(3thioxo-3H-1,2,4-dithiazol-5-yl)acetoamide (Compound 2) (0.187 g, 18%).

Workup

  1. stirringAfter being stirred for 3 hours at room temperature
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe obtained residue was purified by silica gel chromatography (chloroform)

Sources & evidence

ORD record
ord-40dff7633b5942c5bf6f11d6c1f0f618
Source dataset
uspto-grants-2008_03
Patent number
US07348017B2

Reaction notes

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