Phenyl isocyanate → JNJ 1661010

HRID 2262904Notes

Reaction equation

HRID 2262904 reaction equation
[C:1]1([C:7]2[N:11]=[C:10]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[S:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:25]1([N:31]=[C:32]=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(OC(C)C)(C)C>O1CCCC1>[C:25]1([NH:31][C:32]([N:15]2[CH2:16][CH2:17][N:12]([C:10]3[S:9][N:8]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:11]=3)[CH2:13][CH2:14]2)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 7672Phenyl isocyanateHCID 7914Diisopropyl EtherHCID 8471TriethylamineHCID 27777601-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazine

Product 1

HCID 2809273JNJ 1661010Yield 80.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (1.00 g, 4.06 mmol) and triethylamine (0.565 ml, 4.06 mmol) in tetrahydrofuran (20 ml) was added, under ice-cooling, phenyl isocyanate (0.529 ml, 4.87 mmol), and the mixture was stirred at room temperature for 3 hours. To the reaction mixture was added diisopropyl ether (40 ml), and the solid was separated by filtration. The resulting solid was recrystallized from a mixed solvent of hexane and ethyl acetate to give 1.19 g (80.4%) of the desired product as a solid.

Workup

  1. temperaturecooling
  2. customthe solid was separated by filtration
  3. customThe resulting solid was recrystallized from a mixed solvent of hexane and ethyl acetate

Sources & evidence

ORD record
ord-ff8368efe46c4697b4610c2eb607286e
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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