Phenylacetyl chloride → N-Hexyl-N-(5-methyl-1,3,4-thiadiazol-2-yl)-2-phenylacetamide

HRID 261795Notes

Reaction equation

HRID 261795 reaction equation
[CH3:1][C:2]1[S:6][C:5]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[N:4][N:3]=1.C(N(CC)CC)C.[C:21]1([CH2:27][C:28](Cl)=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1(C)C=CC=CC=1>[CH2:8]([N:7]([C:5]1[S:6][C:2]([CH3:1])=[N:3][N:4]=1)[C:28](=[O:29])[CH2:27][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 7679Phenylacetyl chloride2×HCID 8471Triethylamine2×HCID 21315314N-Hexyl-5-methyl-1,3,4-thiadiazol-2-amine

Product 1

HCID 21679768N-Hexyl-N-(5-methyl-1,3,4-thiadiazol-2-yl)-2-phenylacetamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-(5-Methyl-1,3,4-thiadiazol-2-yl)-hexylamine (5.98 g, 0.03 mole) in toluene (60 ml) was stirred together with triethylamine (4.59 ml) and phenylacetyl chloride (4.64 g, 0.03 mole) and refluxed overnight. Further triethylamine (4.6 ml) and phenylacetyl chloride (4 ml) were added and refluxing was continued for a further 24 hours. The mixture was evaporated to dryness, treated with water and extracted with chloroform. The chloroform extract was washed with 2N sodium hydroxide solution and with water, and was dried (Na2SO4), filtered and evaporated to yield the title product as an oil, b.p. 190° C./0.1 mm (8.03 g). This was recrystallised from ethanol to give the title compound as a solid, m.p. 90° C.

Workup

  1. temperaturerefluxed overnight
  2. temperaturerefluxing
  3. customThe mixture was evaporated to dryness
  4. additiontreated with water
  5. extractionextracted with chloroform
  6. extractionThe chloroform extract
  7. washwas washed with 2N sodium hydroxide solution and with water
  8. dry with materialwas dried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-07d9c8aab9f147bb90a196f863636bce
Source dataset
uspto-grants-1979_05
Patent number
US04152442

Reaction notes

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