Water → HCID 14053142, compound

HRID 2107104Notes

Reaction equation

HRID 2107104 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([OH:18])[C:10]=2[CH2:19][CH2:20][CH3:21])=[N:5][N:6]=1.CC[C:24]([C:26](Cl)=[O:27])=[O:25].[OH2:29].N1[CH:35]=[CH:34]C=CC=1>>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([CH2:8][S:7][C:4]2[S:3][C:2]([NH:1][C:24](=[O:25])[C:26]([O:27][CH2:34][CH3:35])=[O:29])=[N:6][N:5]=2)=[C:10]([CH2:19][CH2:20][CH3:21])[C:11]=1[OH:18])(=[O:17])[CH3:16]

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 11007880Butanoyl chloride, 2-oxo-HCID 14053129HCID 14053129, compound

Product 1

HCID 14053142HCID 14053142, compound

Procedure

To a solution of 0.30 g of 2-amino-5-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-1,3,4-thiadiazole obtained in Example 5 in 6.5 ml of pyridine was dropwise added 0.20 g of ethyloxalyl chloride at -30° C. The mixture was stirred at room temperature for 30 minutes. Water was added to the reaction mixture followed by extraction with ethyl acetate After the extract was dried over anhydrous magnesium sulfate, the solvent was distilled off. The residue was subjected to silica gel column chromatography. Elution with a solvent mixture of chloroform-ethyl acetate (8:1) gave 0.15 g of ethyl [5-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]- 1,3,4-thiadiazol-2-yl]oxamate.

Workup

  1. customat -30° C
  2. extractionfollowed by extraction with ethyl acetate After the extract
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. washElution
  6. additionwith a solvent mixture of chloroform-ethyl acetate (8:1)

Sources & evidence

ORD record
ord-7a39a8b034944fad93a26fc6127ddb72
Source dataset
uspto-grants-1990_06
Patent number
US04933348

Reaction notes

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