Thiophosgene → HCID 21390724, compound

HRID 2397868Notes

Reaction equation

HRID 2397868 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([C:13]3[O:14][CH:15]=[CH:16][CH:17]=3)[N:9]=2)=[CH:4][C:3]=1[NH2:18].[C:19](Cl)(Cl)=[S:20]>O1CCCC1.C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([C:13]3[O:14][CH:15]=[CH:16][CH:17]=3)[N:9]=2)=[CH:4][C:3]=1[N:18]=[C:19]=[S:20]

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 21390701HCID 21390701, compound

Product 1

HCID 21390724HCID 21390724, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4.8 g of 5-(4-chloro-3-aminophenyl)-3-(2-furyl)-1,2,4-oxadiazole in 400 ml of tetrahydrofuran, 5 ml of triethylamine and 2.1 g of thiophosgene are added. After stirring at room temperature for 4 hours, the reaction mixture is filtered and evaporated to dryness in vacuo. The residue is crystallized from petroleum ether to yield 1.5 g (27%) of the title product, m.p. 131°-132° .

Workup

  1. filtrationthe reaction mixture is filtered
  2. customevaporated to dryness in vacuo
  3. customThe residue is crystallized from petroleum ether

Sources & evidence

ORD record
ord-2bec01ed99ce4e93a7e283fec898d518
Source dataset
uspto-grants-1977_05
Patent number
US04022901

Reaction notes

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