1-Indanone → 1H-Indene-2-carbothioamide, 2,3-dihydro-1-oxo-N-phenyl-

HRID 1714429Notes

Reaction equation

HRID 1714429 reaction equation
[H-].[Na+].[C:3]1(=[O:12])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4]1.[C:13]1([N:19]=[C:20]=[S:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH4+].[Cl-]>C1COCC1>[C:13]1([NH:19][C:20]([CH:4]2[CH2:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:3]2=[O:12])=[S:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 67351-IndanoneHCID 7673Phenyl IsothiocyanateHCID 24758Sodium hydrideHCID 25517Ammonium Chloride

Product 1

HCID 109674881H-Indene-2-carbothioamide, 2,3-dihydro-1-oxo-N-phenyl-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (60% dispersion in mineral oil, 0.25 g, 6 mmol) and indan-1-one, Compound 1a, (0.50 g, 3.79 mmole) in THF (5 mL) were mixed under argon. The mixture was stirred at ambient temperature for 5 min. Then, phenylisothiocyanate, Compound 1b, (0.46 mL, 3.79 mmole) was added to the mixture. After an additional 5 min, the reaction was completed as shown by TLC analysis and the reaction mixture was poured into NH4Cl solution and then filtered subsequently. 1-Oxo-indan-2-carbothioic acid phenylamide (Intermediate A), was crystallized from CH3CN as a yellow solid. MS m/z 268 (M+H)+; 1H NMR (DMSO-d6):3.5 (dd, 0.3H), 3.8 (d, 0.15H), 3.9 (s, 1.55H), 4.3 (dd, 0.3H), 7.3 (t, 1H), 7.4-7.8 (m, 7.4H), 7.9 (d, 0.6H), 10.6 (s, 0.7H), 12.1 (s, 0.3H), 14.1 (s, 0.7H).

Workup

  1. waitAfter an additional 5 min
  2. filtrationfiltered subsequently
  3. custom1-Oxo-indan-2-carbothioic acid phenylamide (Intermediate A), was crystallized from CH3CN as a yellow solid

Sources & evidence

ORD record
ord-cfd07828fd6847879d1c9dc696e7515c
Source dataset
uspto-grants-2010_09
Patent number
US07795440B2

Reaction notes

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