Potassium Carbonate → HCID 54533967, compound

HRID 442905Notes

Reaction equation

HRID 442905 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]([F:29])([F:28])[F:27])(=[O:19])=[O:18])[CH:12]=[C:13]([CH3:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([N:16]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]([F:29])([F:28])[F:27])(=[O:19])=[O:18])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH:12]=[C:13]([CH3:15])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 117544Ethyl 6-bromohexanoateHCID 54501570HCID 54501570, compound

Product 1

HCID 54533967HCID 54533967, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

3-Benzyloxy-5-methyl-1-(2-trifluoromethylphenylsulfonylamino)benzene (550 mg, 1.3 mmol), as prepared in the preceding step, ethyl 6-bromohexanoate (290 mg, 1.3 mmol), and K2CO3 (1.0 g) were mixed in N,N-dimethylformamide (10 mL). The mixture was heated to 60° C. and stirred for 12 h. The solid was removed by filtration, and the filtrate was evaporated under high vacuum. The residue was dissolved in ethyl acetate (100 mL), washed with saturated aqueous NaHCO3 (2×50 mL) and brine (2×50 mL), and dried over Na2SO4. The solvent was evaporated in vacuo to give the title compound as a pale red oil (735 mg, 100%) which was directly used for the next step. 1H-NMR (300 MHz, CDCl3) δ 7.85 (d, J=7.7 Hz, 1 H), 7.71 (d, J=7.8 Hz, 1 H), 7.60 (t, J=7.7 Hz, 1 H), 7.47 (t, J=7.7 Hz, 1 H), 7.37 (m, 5 H), 6.71 (s, 1 H), 6.53 (s, 1 H), 6.51 (s, 1 H), 4.95 (s,2H), 4.11 (q, J=7.1 Hz, 2 H),3.66(t,J=7.0 Hz, 2 H), 2.25 (t, J=7.4 Hz, 2 H), 2.23 (s, 3 H), 1.33-1.62 (m, 6 H), 1.24 (t, J=7.1 Hz, 3 H).

Workup

  1. customThe solid was removed by filtration
  2. customthe filtrate was evaporated under high vacuum
  3. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  4. washwashed with saturated aqueous NaHCO3 (2×50 mL) and brine (2×50 mL)
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-5c8949ba7e5b49b2938cb292822b5968
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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