Water → N-Hexyl-5-methyl-1,3,4-thiadiazol-2-amine

HRID 236897Notes

Reaction equation

HRID 236897 reaction equation
[CH3:1][C:2]1[S:6][C:5]([NH:7][C:8](=O)[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[N:4][N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[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

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 5097025N-(5-methyl-1,3,4-thiadiazol-2-yl)hexanamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 21315314N-Hexyl-5-methyl-1,3,4-thiadiazol-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-(5-Methyl-1,3,4-thiadiazol-2-yl)-hexanamide (16 g, 0.075 mole) was added portionwise to stirred tetrahydrofuran (THF) (120 ml) containing lithium aluminium hydride (2.9 g, 0.076 mole) at a temperature below 15° C. The mixture was stirred and refluxed for 2 hours. The mixture was cooled in ice and treated with water (2.9 ml) in THF (29 ml) followed by a 2 N solution of sodium hydroxide (2.9 ml) and water (5.8 ml). The mixture was then treated with `Supercel` and filtered. The filtrate was evaporated to give the title product which was recrystallised from 50% aqueous methanol (9.5 g) m.p. 101°-105° C.

Workup

  1. temperaturerefluxed for 2 hours
  2. temperatureThe mixture was cooled in ice
  3. additionThe mixture was then treated with `Supercel` and
  4. filtrationfiltered
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-f9d1c27fd3d845abb40d085ef81b1d95
Source dataset
uspto-grants-1979_06
Patent number
US04158659

Reaction notes

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