63413-91-2 → HCID 68488496, compound

HRID 1882338Notes

Reaction equation

HRID 1882338 reaction equation
[C:1]1([S:7][CH:8]=[CH:9][C:10]([OH:12])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:13][C:14]1[S:18][C:17]([S:19][CH3:20])=[N:16][CH:15]=1>C(#N)C.C(N(CC)CC)C>[CH3:20][S:19][C:17]1[S:18][C:14]([NH:13][C:10](=[O:12])[CH:9]=[CH:8][S:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:15][N:16]=1

Participants

5

Reactant 2

HCID 27570663413-91-2HCID 132489052-(Methylsulfanyl)-1,3-thiazol-5-amine

Product 1

HCID 68488496HCID 68488496, compoundYield 30.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of 3-(phenylthio)acrylic acid (3.69 g) in acetonitrile (50 mL) were added a solution of 5-amino-2-(methylthio)thiazole (3.00 g) in acetonitrile (10 mL) and triethylamine (2.80 mL) under ice-cooling. The mixture was stirred at the same temperature for 2 hours and then at room temperature for 3 hours, and then concentrated under reduced pressure. To the residue was added 1N hydrochloric acid (50 mL), which was extracted with ethyl acetate (100 mL) twice. The organic layers were combined, washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain N-[2-(methylthio)thiazol-5-yl]-3-(phenylthio)acrylamide (1.90 g) as a dark yellow crystal.

Workup

  1. temperaturecooling
  2. waitat room temperature for 3 hours
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue was added 1N hydrochloric acid (50 mL), which
  5. extractionwas extracted with ethyl acetate (100 mL) twice
  6. washwashed with water
  7. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9eecd080a22147d9806460c5a3f6c1f6
Source dataset
uspto-grants-2012_11
Patent number
US08318981B2

Reaction notes

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