Benzoyl isothiocyanate → HCID 86672763, compound

HRID 1754958Notes

Reaction equation

HRID 1754958 reaction equation
[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:12][C:13]1[CH:18]=[C:17]([NH:19][CH3:20])[CH:16]=[C:15]([CH3:21])[C:14]=1[CH2:22][CH2:23][S:24]([N:27]1[CH2:44][CH2:43][C:30]2([N:34]=[C:33]([CH:35]3[CH2:40][CH2:39][CH:38]([CH3:41])[CH2:37][CH2:36]3)[NH:32][C:31]2=[O:42])[CH2:29][CH2:28]1)(=[O:26])=[O:25]>CC(C)=O>[C:1]([NH:9][C:10](=[S:11])[N:19]([C:17]1[CH:18]=[C:13]([CH3:12])[C:14]([CH2:22][CH2:23][S:24]([N:27]2[CH2:28][CH2:29][C:30]3([N:34]=[C:33]([CH:35]4[CH2:40][CH2:39][CH:38]([CH3:41])[CH2:37][CH2:36]4)[NH:32][C:31]3=[O:42])[CH2:43][CH2:44]2)(=[O:26])=[O:25])=[C:15]([CH3:21])[CH:16]=1)[CH3:20])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 66816789HCID 66816789, compound

Product 1

HCID 86672763HCID 86672763, compoundYield 104.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzoyl isothiocyanate (37.8 mg, 0.23 mmol) was added to a solution of 8-[2-(2,6-dimethyl-4-methylamino-phenyl)-ethanesulfonyl]-2-(4-methyl-cyclohexyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (100 mg, 0.21 mmol) in acetone (3 ml) in a nitrogen stream. The mixture was heated under reflux for one hour and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane-methanol) to give 3-benzoyl-1-(3,5-dimethyl-4-{2-[2-(4-methyl-cyclohexyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-phenyl)-1-methyl-thiourea (140 mg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for one hour
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (dichloromethane-methanol)

Sources & evidence

ORD record
ord-f239385dfc234aeb8ebf8c7ed1549e9e
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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