Benzoyl chloride → HCID 25096340, compound

HRID 1015430Notes

Reaction equation

HRID 1015430 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S-:10][C:11]#[N:12].[NH4+].[Cl:14][C:15]1[CH:36]=[CH:35][C:18]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH:34]=[CH:33][CH:32]=[C:31]3[C:27]=2[CH2:28][CH2:29][NH:30]3)=[CH:17][CH:16]=1>CC(C)=O>[Cl:14][C:15]1[CH:36]=[CH:35][C:18]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH:34]=[CH:33][CH:32]=[C:31]3[C:27]=2[CH2:28][CH2:29][N:30]3[C:11]([NH:12][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[S:10])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 67300937HCID 67300937, compound

Product 1

HCID 25096340HCID 25096340, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of benzoyl chloride (42 mg, 0.3 mmol) in acetone (3.0 mL) was added ammonium thiocyanate (68 mg, 0.9 mmol). The resulting mixture was stirred for 1 h at room temperature followed by addition of the indoline compound 4-[5-(4-chloro-phenoxy)-pentyloxy]-2,3-dihydro-1H-indole (100 mg, 0.3 mmol). After stirred overnight at room temperature, the reaction mixture was quenched with excess saturated ammonium chloride (30 mL) and extracted with ethyl acetate (30 mL×3). The organic layers were combined, washed with brine, and then concentrated under vacuum. The residue was purified by silica gel chromatography to give N-{4-[5-(4-chloro-phenoxy)-pentyloxy]-2,3-dihydro-indole-1-carbothioyl}-benzamide (74 mg, 0.15 mmol, 50%) as a white solid. MS (EI): m/z 495 (M+H).

Workup

  1. stirringAfter stirred overnight at room temperature
  2. customthe reaction mixture was quenched with excess saturated ammonium chloride (30 mL)
  3. extractionextracted with ethyl acetate (30 mL×3)
  4. washwashed with brine
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-2466bd3ae0b84676bb5d731205d120cf
Source dataset
uspto-grants-2011_07
Patent number
US07985763B2

Reaction notes

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