Water → HCID 68420965, compound

HRID 506435Notes

Reaction equation

HRID 506435 reaction equation
[CH:1]1([C:4]2(C(O)=O)[CH2:8][S:7][N:6]=[N:5]2)[CH2:3][CH2:2]1.Cl.C(N=C=[N:17][CH2:18][CH2:19][CH2:20][N:21]([CH3:23])C)C.[C:24]([C:26]1C=CC=[CH:29][C:27]=1N)#N.[OH2:33]>C1COCC1>[C:18]([C:19]1[CH:29]=[CH:27][CH:26]=[CH:24][C:20]=1[NH:21][C:23]([C:8]1[S:7][N:6]=[N:5][C:4]=1[CH:1]1[CH2:2][CH2:3]1)=[O:33])#[N:17]

Participants

6

Reactant 4

HCID 962WaterHCID 729132-AminobenzonitrileHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68422664HCID 68422664, compound

Product 1

HCID 68420965HCID 68420965, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Cyclopropyl-1,2,3-thiadiazolecarboxylic acid (0.5 g; 2.9 mmols), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (0.62 g; 3.2 mmols) and 2-cyanoaniline (0.38 g; 3.2 mmols) were dissolved or suspended in THF (15 ml), followed by stirring at room temperature for 10 hours. Subsequently, water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with successively a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution. After drying over anhydrous magnesium sulfate, the solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to thereby obtain 0.53 g of 2′-cyano-4-cyclopropyl-1,2,3-thiadiazole-5-carboxanilide.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with successively a saturated aqueous sodium hydrogencarbonate solution
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. concentrationthe solution was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-f63b6a0b34ec424d86dcfd9f82e2f6d9
Source dataset
uspto-grants-2010_08
Patent number
US07786040B2

Reaction notes

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