Benzoyl isothiocyanate → HCID 58930347, compound

HRID 2360279Notes

Reaction equation

HRID 2360279 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]23[CH2:18][CH2:17][C:14]([NH2:19])([CH2:15][CH2:16]2)[CH2:13][CH2:12]3)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:20]([N:28]=[C:29]=[S:30])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[C:20]([NH:28][C:29]([NH:19][C:14]12[CH2:17][CH2:18][C:11]([C:8]3[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=3)([CH2:16][CH2:15]1)[CH2:12][CH2:13]2)=[S:30])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 58930118HCID 58930118, compound

Product 1

HCID 58930347HCID 58930347, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 100 mL round-bottomed flask equipped with magnetic stirring was added 4-(4-(methylsulfonyl)phenyl)bicyclo[2.2.2]octan-1-amine (120 mg, 429 μmol) in 2 mL of CH2Cl2, and benzoyl isothiocyanate (63.6 μl, 472 μmol). The reaction was stirred at ambient temperature for ca. 26 h, and then it was concentrated in vacuo to give 1-benzoyl-3-(4-(4-(methylsulfonyl)phenyl)bicyclo[2.2.2]octan-1-yl)thiourea (mass=185 mg, Mass spec. m/z+ion=443.2). The crude reaction product was taken onto the next step without further purification.

Workup

  1. customTo a 100 mL round-bottomed flask equipped
  2. stirringThe reaction was stirred at ambient temperature for ca. 26 h
  3. concentrationit was concentrated in vacuo

Sources & evidence

ORD record
ord-fa556e4801fb4772961604e4a244fa92
Source dataset
uspto-grants-2014_04
Patent number
US08686011B2

Reaction notes

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