1,1'-Thiocarbonyldiimidazole → (5-tert-butyl-1H-pyrazole-3-yl)-thiourea

HRID 1971470Notes

Reaction equation

HRID 1971470 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[NH:4][N:3]=1.[C:11](N1C=CN=C1)([N:13]1C=CN=C1)=[S:12].C([O-])(=O)C.[NH4+]>C(#N)C>[C:7]([C:5]1[NH:4][N:3]=[C:2]([NH:1][C:11]([NH2:13])=[S:12])[CH:6]=1)([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 517165Ammonium AcetateHCID 5227873-Amino-5-tert-butylpyrazole

Product 1

HCID 86761819(5-tert-butyl-1H-pyrazole-3-yl)-thiourea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

1.5 g (11.3 mmol) 3-amino-5-tert-butylpyrazole dissolved in acetonitrile, was added drop-wise and slowly to a solution of 2.0 g (11.3 mmol) thiocarbonyldiimidazole in 25 ml acetonitrile, at 0° C. The batch was stirred for 20 minutes at 0° C., ammonium acetate (1.6 g, 21.5 mmol) was then added, and the mixture was heated in the microwave for 30 minutes at 90° C. (radiation power 200 Watt/without cooling). The solid formed was suction-isolated, the solution was concentrated and the oily residue (4.3 g) was crudely purified on silica gel (0.9 g yellowish solid)

Workup

  1. additionwas added drop-wise
  2. customat 0° C
  3. temperaturethe mixture was heated in the microwave for 30 minutes at 90° C.
  4. temperature(radiation power 200 Watt/without cooling)
  5. customThe solid formed
  6. customwas suction-isolated
  7. concentrationthe solution was concentrated
  8. customthe oily residue (4.3 g) was crudely purified on silica gel (0.9 g yellowish solid)

Sources & evidence

ORD record
ord-3dc5bac6ffb3496f8e2b0fdb6833b440
Source dataset
uspto-grants-2013_04
Patent number
US08431604B2

Reaction notes

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