Water → HCID 66751070, compound

HRID 535005Notes

Reaction equation

HRID 535005 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=2)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].Cl[CH2:27][CH2:28][N:29]=[C:30]=[O:31].[H-].[Na+].O>O1CCCC1>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][N:14]([C:17]([C:19]2[CH:25]=[CH:24][C:22]([N:23]3[CH2:27][CH2:28][NH:29][C:30]3=[O:31])=[CH:21][CH:20]=2)=[O:18])[CH2:15][CH2:16]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 160352-Chloroethyl isocyanateHCID 24758Sodium hydrideHCID 66792770HCID 66792770, compound

Product 1

HCID 66751070HCID 66751070, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}aniline (1.1 g, 3.26 mmol) and 2-chloroethyl isocyanate (0.369 g, 3.5 mmol) in tetrahydrofuran (15 mL) was stirred at room temperature for overnight. Sodium hydride was added to the reaction mixture and the mixture was stirred at room temperature for 3 h. Water was added to the reaction solution, and the resulting solid was collected and washed with water, diethyl ether, dried over anhydrous magnesium sulfate, and dried under reduced pressure to give the title compound as a solid (1.2 g, 91%).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 h
  2. customthe resulting solid was collected
  3. washwashed with water, diethyl ether
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-01f85b2ed32e438cbd0c9cf6e11de8ef
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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