Triethylamine → HCID 21387500, compound

HRID 1833806Notes

Reaction equation

HRID 1833806 reaction equation
[CH2:1]([O:3][C:4]([N:6]=[C:7]=[O:8])=[O:5])[CH3:2].[OH:9][C:10]1[N:14]=[C:13]([O:15][CH2:16][CH3:17])[S:12][N:11]=1.C(N(CC)CC)C>O1CCCC1>[CH2:1]([O:3][C:4]([NH:6][C:7]([N:11]1[C:10](=[O:9])[N:14]=[C:13]([O:15][CH2:16][CH3:17])[S:12]1)=[O:8])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 300166ethyl N-carbonylcarbamateHCID 178467476HCID 178467476, compound

Product 1

HCID 21387500HCID 21387500, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

23 g of ethoxycarbonyl isocyanate were added dropwise to a solution of 14.6 g of 3-hydroxy-5-ethoxy-1,2,4-thiadiazole in 140 ml of tetrahydrofuran containing 1 ml of triethylamine and the mixture was stirred for 11/2 hours at 20° C and was filtered. The filtrate was concentrated to dryness and the residue was empasted with isopropyl ether and vacuum filtered. The product was crystallized from ethyl acetate to obtain 18 g of 2-(N-ethoxycarbonylcarbamoyl)-5-ethoxy-1,2,4-thiadiazole-3-one melting at 119° C.

Workup

  1. filtrationwas filtered
  2. concentrationThe filtrate was concentrated to dryness
  3. filtrationfiltered
  4. customThe product was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-c2ff21330bf944f3a6e175e2fd5bd7b5
Source dataset
uspto-grants-1978_01
Patent number
US04067720

Reaction notes

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