1-Chloro-2-(diethylamine)ethane hydrochloride → 5-{[2-(Diethylamino)ethyl]sulfanyl}-1,3,4-thiadiazol-2-amine

HRID 1416216Notes

Reaction equation

HRID 1416216 reaction equation
[NH2:1][C:2]1[S:3][C:4]([SH:7])=[N:5][N:6]=1.Cl.[CH2:9]([N:11]([CH2:14][CH2:15]Cl)[CH2:12][CH3:13])[CH3:10].[OH-].[K+]>CO>[NH2:1][C:2]1[S:3][C:4]([S:7][CH2:10][CH2:9][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[N:5][N:6]=1

Participants

5

Reactant 3

HCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 14797Potassium HydroxideHCID 178509208HCID 178509208, compound

Product 1

HCID 3145445-{[2-(Diethylamino)ethyl]sulfanyl}-1,3,4-thiadiazol-2-amineYield 81.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Amino-5-mercapto-1,3,4-thiadiazole (13.3 g), diethylaminoethylchloridehydrochloride (17.2 g), and potassium hydroxide (11.2 g) were stirred in methanol (200 ml) overnight at room temperature. The reaction mixture was concentrated under a vacuum. The residue, with water added thereto, was extracted with ethyl acetate. The extract was dried over sodium sulfate anhydride, and then concentrated under a vacuum. The resulting solid was recrystallized from n-hexane/ethanol, thereby yielding 19.0 g of the aimed compound.

Workup

  1. concentrationThe reaction mixture was concentrated under a vacuum
  2. additionThe residue, with water added
  3. extractionwas extracted with ethyl acetate
  4. dry with materialThe extract was dried over sodium sulfate anhydride
  5. concentrationconcentrated under a vacuum
  6. customThe resulting solid was recrystallized from n-hexane/ethanol

Sources & evidence

ORD record
ord-fa9b5c1a0a2d44cb88db190db0e2200d
Source dataset
uspto-grants-1999_06
Patent number
US05912258

Reaction notes

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