Ammonium thiocyanate → HCID 25096337, compound

HRID 1015426Notes

Reaction equation

HRID 1015426 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[S-:11][C:12]#[N:13].[NH4+].[C:15]1([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][O:31][C:32]2[CH:41]=[CH:40][CH:39]=[C:38]3[C:33]=2[CH2:34][CH2:35][CH2:36][NH:37]3)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1>CC(C)=O>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:13][C:12]([N:37]2[C:38]3[C:33](=[C:32]([O:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][O:25][C:15]4[C:24]5[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=5)[CH:18]=[CH:17][CH:16]=4)[CH:41]=[CH:40][CH:39]=3)[CH2:34][CH2:35][CH2:36]2)=[S:11])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 15666Ammonium thiocyanateHCID 678794-Fluorobenzoyl chlorideHCID 67300903HCID 67300903, compound

Product 1

HCID 25096337HCID 25096337, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 4-fluorobenzoyl chloride (38 mg, 0.24 mmol) in acetone (2.0 mL) was added ammonium thiocyanate (51 mg, 0.66 mmol). The resulting mixture was stirred for 1 h at room temperature followed by the addition of the above-obtained tetrahydroquinoline compound (80 mg, 0.22 mmol). After stirred overnight at room temperature, the reaction mixture was quenched with excess saturated ammonium chloride (20 mL) followed by extraction with ethyl acetate (3×20 L). The organic layers were combined, washed with brine, and then concentrated under vacuum. The residue was purified by silica gel chromatography to give 4-fluoro-N-{5-[5-(naphthalen-1-yloxy)-pentyloxy]-3,4-dihydro-2H-quinoline-1-carbothioyl}-benzamide (83 mg, 0.15 mmol, 70%) as a white solid. MS (EI): m/z 543 (M+H).

Workup

  1. stirringAfter stirred overnight at room temperature
  2. customthe reaction mixture was quenched with excess saturated ammonium chloride (20 mL)
  3. extractionfollowed by extraction with ethyl acetate (3×20 L)
  4. washwashed with brine
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-74109ca3df184a68bd7192e84aab54d4
Source dataset
uspto-grants-2011_07
Patent number
US07985763B2

Reaction notes

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