Benzyl isocyanate → HCID 27533560, compound

HRID 1841948Notes

Reaction equation

HRID 1841948 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:19]([N:26]=[C:27]=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>N1C=CC=CC=1>[CH2:19]([NH:26][C:27]([N:16]1[CH2:17][CH2:18][N:13]([S:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)(=[O:12])=[O:11])[CH2:14][CH2:15]1)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 2410357HCID 2410357, compound

Product 1

HCID 27533560HCID 27533560, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-(4-Nitro-benzenesulfonyl)-piperazine (1.0 g, 2.6 mmol) in pyridine (10 ml) was added benzyl isocyanate (0.35 ml, 2.85 mmol) in one portion. The resulting mixture was then heated at 50° C. for 2 hours before being cooled to room temperature and concentrated under vacuum. The resulting residue was dissolved in ethyl acetate (50 ml) and washed with 1M HCl (100 ml), the organic layer was separated, dried (MgSO4), filtered and concentrated under vacuum to give the title compound (0.5 g, 47% yield) as a yellow solid which was used without further purification. Tr=1.86 min, m/z (ES+) (M+H)+ 405.

Workup

  1. temperaturebefore being cooled to room temperature
  2. concentrationconcentrated under vacuum
  3. dissolutionThe resulting residue was dissolved in ethyl acetate (50 ml)
  4. washwashed with 1M HCl (100 ml)
  5. customthe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b6a90d854fe64ae191b9d99af008d299
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Reaction notes

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