Ammonia → 3-Benzyl-1,2,4-thiadiazol-5-amine

HRID 2063669Notes

Reaction equation

HRID 2063669 reaction equation
[CH2:1]([C:8]1[N:12]=[C:11](Cl)[S:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:14]>>[CH2:1]([C:8]1[N:12]=[C:11]([NH2:14])[S:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 147635213-Benzyl-5-chloro-1,2,4-thiadiazole

Product 1

HCID 6055933-Benzyl-1,2,4-thiadiazol-5-amine

Conditions

Temperature
50 °C

Procedure

A mixture of 3-benzyl-5-chloro-[1,2,4]thiadiazole (105 mg, 0.5 mmol) in ammonia (2 N in MeOH, 2 ml) was heated in a pressure tube at 50° C. for 5 h. The solvents were evaporated, the residue diluted with dichloromethane, the white solid (ammonium chloride) was filtered off, the filtrate was concentrated and then purified by silica gel chromatography using dichloromethane/methanol as eluent. The title compound was obtained as a light yellow liquid (40 mg, 41%). MS ISP (m/e): 192.1 (100) [(M+H)+].

Workup

  1. customThe solvents were evaporated
  2. additionthe residue diluted with dichloromethane
  3. filtrationthe white solid (ammonium chloride) was filtered off
  4. concentrationthe filtrate was concentrated
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-627c223dfef649a5a6faf340263f78f3
Source dataset
uspto-grants-2012_10
Patent number
US08288403B2

Reaction notes

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