Butyl Isothiocyanate → HCID 19778068, compound

HRID 2082314Notes

Reaction equation

HRID 2082314 reaction equation
[N:1]1([C:6]2[CH:20]=[CH:19][C:9]([C:10]([N:12]3[CH2:17][CH2:16][CH:15]([NH2:18])[CH2:14][CH2:13]3)=[O:11])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[CH2:21]([N:25]=[C:26]=[S:27])[CH2:22][CH2:23][CH3:24]>C(Cl)Cl>[CH2:21]([NH:25][C:26]([NH:18][CH:15]1[CH2:16][CH2:17][N:12]([C:10](=[O:11])[C:9]2[CH:8]=[CH:7][C:6]([N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)=[CH:20][CH:19]=2)[CH2:13][CH2:14]1)=[S:27])[CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 11613Butyl Isothiocyanate2×HCID 19778044HCID 19778044, compound

Product 1

HCID 19778068HCID 19778068, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[4-(1H-Imidazol-1-yl)benzoyl]-4-piperidinamine (4.06 g, 15.0 mmol) and butyl isothiocyanate (1.81 mL, 1.73 g, 15.0 mmol) are combined in methylene chloride (75 mL) and stirred at room temperature. After 24 hr, an additional portion (0.90 mL, 0.86 g, 7.5 mmol) of butyl isothiocyanate is added, and the mixture is stirred for 48 hr. The mixture is washed twice with 1N aqueous sodium hydroxide, once with brine, dried over magnesium sulfate, and evaporated. Trituration of the residue with ether and recrystallization from ethanol-ether affords the title compound.

Workup

  1. stirringthe mixture is stirred for 48 hr
  2. washThe mixture is washed twice with 1N aqueous sodium hydroxide, once with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customTrituration of the residue with ether and recrystallization from ethanol-ether

Sources & evidence

ORD record
ord-bdf89b4e336e49449c3987520f187e9f
Source dataset
uspto-grants-1993_02
Patent number
US05189036

Reaction notes

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