Ethanol → HCID 67908627, compound

HRID 1533857Notes

Reaction equation

HRID 1533857 reaction equation
Br[C:2]1[S:3][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:5][N:6]=1.[CH2:13]([N:15]([CH2:21][CH3:22])[C:16]#[C:17][CH:18]([NH2:20])[CH3:19])[CH3:14].C([OH:25])C>>[OH2:25].[CH2:13]([N:15]([CH2:21][CH3:22])[C:16]#[C:17][CH:18]([NH:20][C:2]1[S:3][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:5][N:6]=1)[CH3:19])[CH3:14]

Participants

4

Reactant 3

HCID 702EthanolHCID 131041172-Bromo-5-phenyl-1,3,4-thiadiazoleHCID 54256340HCID 54256340, compound

Product 1

HCID 67908627HCID 67908627, compound

Procedure

4 g of 2-bromo 5-phenyl-1,3,4-thiadiazole prepared as indicated in Tetrahedron, 1968, 24, 3214 was mixed with 6.98 g of 4-diethylamino butyn-2-yl amine prepared as indicated in Eur. J. Med. Chem. Chim. Ther., 1982, 17, 85-88. The mixture was reflux-heated in 100 ml of ethanol for 48 hours. The ethanol was concentrated in vacuo, and the residue was dissolved in a 4 N soda solution. It was extracted with ethyl acetate, then the organic phase was washed with water, dried on sodium sulphate and the residual oil was chromatographed on silica gel, using ethylacetate as the eluent.

Workup

  1. customprepared
  2. concentrationThe ethanol was concentrated in vacuo
  3. dissolutionthe residue was dissolved in a 4 N soda solution
  4. extractionIt was extracted with ethyl acetate
  5. washthe organic phase was washed with water
  6. customdried on sodium sulphate
  7. customthe residual oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-8183f601379d4bdaaf9fca0543aeffa4
Source dataset
uspto-grants-1992_02
Patent number
US05086053

Reaction notes

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