Benzoyl chloride → HCID 11432126, compound

HRID 2266951Notes

Reaction equation

HRID 2266951 reaction equation
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][C:15]([N:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][O:25][CH2:26][CH2:27][OH:28])[CH2:19][CH2:18]2)=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:36](Cl)(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[C:1]1([S:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][C:15]([N:17]2[CH2:18][CH2:19][N:20]([CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][C:36](=[O:43])[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH2:21][CH2:22]2)=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 11486440HCID 11486440, compound

Product 1

HCID 11432126HCID 11432126, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
20 °C

Procedure

4-[2-(2-hydroxyethoxy)-ethyl]-piperazine-carboxylic acid (2-phenylsulfanyl-phenyl)-amide (4 g, 10 mmol), triethylamine (2 ml, 15 mmol) and toluene (50 ml) were charged into a reaction flask. Benzoyl chloride (1.7 g, 12 mmol) in toluene (5 ml) was added at 0-10° C. The mixture was stirred for 16 h at 20° C. Cold water (50 ml) and 1 M NaOH (100 ml) were added. The mixture was stirred for 20 min. The water phase was separated. The organic phase was washed with saturated NaCl solution (25 ml) and evaporated in vacuo. The yield of benzoic acid 2-{2-[4-(2-phenylsulfanyl-phenylcarbamoyl)piperazin-1-yl]-ethoxy}-ethyl ester was 4.91 g.

Workup

  1. stirringThe mixture was stirred for 20 min
  2. customThe water phase was separated
  3. washThe organic phase was washed with saturated NaCl solution (25 ml)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-e6f811528bd64dec8243e7d9a24b1b5e
Source dataset
uspto-grants-2010_12
Patent number
US07858777B2

Reaction notes

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