Ethyl cyanoformate → HCID 13021999, compound

HRID 967758Notes

Reaction equation

HRID 967758 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[C:9]2OC(=O)[S:11][N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])#[N:16]>>[C:1]1(/[CH:7]=[CH:8]/[C:9]2[N:16]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[S:11][N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 69336Ethyl cyanoformateHCID 13021992HCID 13021992, compound

Product 1

HCID 13021999HCID 13021999, compoundYield 66%

Procedure

5-[(E)-2-Phenylethenyl]-1,3,4-oxathiazol-2-one (1.4 g, 7.0 mmol) was mixed with ethyl cyanoformate (2.4 g, 25 mmol) in xylenes, and heated to reflux for 3 h. The reaction mixture was concentrated in vacuo, and the resulting material was recrystallized from ethyl acetate-ethanol (1:1) to give ethyl 3-[(E)-2-phenylethenyl]-1,2,4-thiadiazole-5-carboxylate (1.2 g, 66% yield) as a light yellow solid. M.p. 79–80° C. 1H NMR (CDCl3, 300 MHz) δ 7.98 (d, J=16 Hz, 1H), 7.61 (m, 2H), 7.40 (m, 3H), 7.29 (d, J=11 Hz, 1H), 4.56 (q, J=7 Hz, 2H), 1.50 (t, J=7 Hz, 3H). MS (EI ionization) 259 (M+−H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe resulting material was recrystallized from ethyl acetate-ethanol (1:1)

Sources & evidence

ORD record
ord-2ae09434a5e1416d830c55ff21f16ba7
Source dataset
uspto-grants-2005_10
Patent number
US06956049B1

Reaction notes

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