Ethyl isocyanate → 5-Butoxy-N-ethyl-3-oxo-1,2,4-thiadiazole-2(3H)-carboxamide

HRID 1833800Notes

Reaction equation

HRID 1833800 reaction equation
C(N(CC)CC)C.[OH:8][C:9]1[N:13]=[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])[S:11][N:10]=1.[CH2:19]([N:21]=[C:22]=[O:23])[CH3:20]>O1CCCC1>[CH2:19]([NH:21][C:22]([N:10]1[C:9](=[O:8])[N:13]=[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])[S:11]1)=[O:23])[CH3:20]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 178450384HCID 178450384, compound

Product 1

HCID 213874995-Butoxy-N-ethyl-3-oxo-1,2,4-thiadiazole-2(3H)-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 ml of triethylamine was added to a solution of 17.4 g of 3-hydroxy-5-n-butoxy-1,2,4-thiadiazole in 150 ml of tetrahydrofuran and then 12 ml of ethyl isocyanate were added dropwise with stirring. The mixture was stirred for 2 hours at 20° C and was concentrated to dryness under reduced pressure. The residue was chromatographed over silica gel and elution with a 7-3 benzene-ethyl acetate mixture yielded 18.5 g of 2-(N-ethylcarbamoyl)-5-n-butoxy-1,2,4-thiadiazole-3-one.

Workup

  1. stirringThe mixture was stirred for 2 hours at 20° C
  2. concentrationwas concentrated to dryness under reduced pressure
  3. customThe residue was chromatographed over silica gel and elution with a 7-3 benzene-ethyl acetate mixture

Sources & evidence

ORD record
ord-aab2f461a2d44d42b8ae11991cd0f98d
Source dataset
uspto-grants-1978_01
Patent number
US04067720

Reaction notes

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