Triethylamine → HCID 54015426, compound

HRID 1833803Notes

Reaction equation

HRID 1833803 reaction equation
C(N(CC)CC)C.[OH:8][C:9]1[N:13]=[C:12]([O:14][CH2:15][CH3:16])[S:11][N:10]=1.[CH2:17]([O:19][CH2:20][CH2:21][N:22]=[C:23]=[O:24])[CH3:18]>O1CCCC1>[CH3:18][CH2:17][O:19][CH2:20][CH2:21][NH:22][C:23]([N:10]1[C:9](=[O:8])[N:13]=[C:12]([O:14][CH2:15][CH3:16])[S:11]1)=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12017510Ethane, 1-ethoxy-2-isocyanato-HCID 178467476HCID 178467476, compound

Product 1

HCID 54015426HCID 54015426, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

1 ml of triethylamine was added to a solution of 14.6 g of 3-hydroxy-5-ethoxy-1,2,4-thiadiazole in 140 ml of tetrahydrofuran and then 23 g of ethoxyethyl isocyanate were added dropwise. The mixture was stirred for 2 hours at 25° C and was concentrated to dryness. The residue was chromatographed over silica gel and elution with a 4-6 benzene-ethyl acetate mixture yielded 14 g of 2-(N-β-ethoxyethylcarbamoyl)-5-ethoxy-1,2,4-thiadiazole-3-one melting at <50° C.

Workup

  1. concentrationwas concentrated to dryness
  2. customThe residue was chromatographed over silica gel and elution with a 4-6 benzene-ethyl acetate mixture

Sources & evidence

ORD record
ord-9213b0f913c043a9ba46597b136890e8
Source dataset
uspto-grants-1978_01
Patent number
US04067720

Reaction notes

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