Water → HCID 86605501, compound

HRID 2103091Notes

Reaction equation

HRID 2103091 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([CH3:14])[C:12]=1[CH3:13])[NH:9][CH2:8][C:7]1([CH2:17][CH2:16][CH2:15]1)[CH2:6]2.[Br:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:25]=[C:26]=[S:27].O>ClCCl>[Br:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][C:26]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:12]([CH3:13])[C:11]=2[CH3:14])[CH2:6][C:7]2([CH2:15][CH2:16][CH2:17]2)[CH2:8]1)=[S:27]

Participants

5

Reactant 3

HCID 962WaterHCID 6116541-Bromo-2-isothiocyanatobenzeneHCID 57803505HCID 57803505, compound

Product 1

HCID 86605501HCID 86605501, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6′-methoxy-7′,8′-dimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinoline] (810 mg) in 4 mL dichloromethane was added 1-bromo-2-isothiocyanatobenzene (525 μL) at room temperature. The mixture was allowed to reflux overnight. Water was used to quench the mixture and EtOAc was used for extraction. The combined organic phases were washed with brine, dried and evaporated. The residue was passed through a column ( dichloromethane:EtOAc=10:2) to give N-(2-bromophenyl)-6′-methoxy-7′,8′-dimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinoline]-1′-carbothioamide (1.5 g) as a white solid. 1H-NMR (300 MHz, CDCl3) δ=8.54-8.22 (d, J=6.95 Hz, 1H); 7.61-7.39 (m, 2H); 7.38-7.22 (m, 1H); 7.15-6.87 (m, 1H); 6.69 (s, 1H); 5.72-5.38 (d, J=13.1 Hz, 1H); 3.86 (s, 3H); 3.39-3.25 (d, J=13.1 Hz, 1H); 2.85-2.67 (m, 2H); 2.46-2.28 (m, 1H); 2.14 (s, 3H); 2.12 (s, 3H); 2.07-1.79 (m, 3H); 1.79-1.62 (m, 2H) ppm.

Workup

  1. temperatureto reflux overnight
  2. customto quench the mixture and EtOAc
  3. extractionwas used for extraction
  4. washThe combined organic phases were washed with brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-c7f1bf813385408895e886cb4fc5dc14
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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