Potassium Carbonate → HCID 46932241, compound

HRID 1192058Notes

Reaction equation

HRID 1192058 reaction equation
Br[CH:2]([C:4]1[S:8][C:7]([S:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])=[C:6]([N+:18]([O-:20])=[O:19])[CH:5]=1)[CH3:3].[CH3:21][O:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH2:28])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:17][C:11]1[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:10]=1[S:9][C:7]1[S:8][C:4]([CH:2]([NH:28][CH2:27][C:26]2[CH:29]=[CH:30][C:23]([O:22][CH3:21])=[CH:24][CH:25]=2)[CH3:3])=[CH:5][C:6]=1[N+:18]([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 754524-MethoxybenzylamineHCID 60207313HCID 60207313, compound

Product 1

HCID 46932241HCID 46932241, compoundYield 11.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-(1-bromoethyl)-2-(2,4-dichlorophenyl)sulfanyl-3-nitro-thiophene (0.8 g, 1.9 mmol), 4-methoxybenzylamine (0.4 mL, 2.85 mmol) and potassium carbonate (0.524 g, 3.8 mmol) were mixed in N,N-dimethylformide (15 mL). The resulting reaction mixture was stirred at ambient temperature for 3 hours. After this time, water was added and the reaction mixture was extracted with ethyl acetate. The organic phase was combined and was washed with brine. The organic layer was separated, dried (Na2SO4), concentrated and purified by preparative TLC using a 4:1 mixture of hexane and ethyl acetate as eluent to afford the title compound (100 mg, 11% yield). 1H NMR (400 MHz, CDCl3) δ: 7.71 (2H, m), 7.64 (2H, m), 7.51 (1H, m), 7.40 (1H, m), 7.11 (1H, m), 6.85 (1H, m), 3.93 (1H, q), 3.83 (3H, s), 3.58 (2H, m), 1.34 (3H, d). MS m/z: 468.9 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washwas washed with brine
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. custompurified by preparative TLC
  8. additiona 4:1 mixture of hexane and ethyl acetate as eluent

Sources & evidence

ORD record
ord-8600e07e37444f9386a7b770b5150cc6
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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