Potassium Carbonate → HCID 86679502, compound

HRID 1776546Notes

Reaction equation

HRID 1776546 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])=[CH:5][C:4]=1[NH:19][S:20]([CH3:23])(=[O:22])=[O:21].Cl[CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])=[CH:5][C:4]=1[N:19]([CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)[S:20]([CH3:23])(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 767274-(2-Chloroethyl)morpholineHCID 86679496HCID 86679496, compound2×

Product 1

HCID 86679502HCID 86679502, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Benzyl 4-methoxy-3-(methylsulfonamido)benzoate (1.5 g, 4.47 mmol, Compound 144 may be prepared in analogous manner as described in Scheme 19, Step 1 and 2) was dissolved in DMF (10 ml), then 4-(2-chloroethyl)morpholine (6.69 g, 44.7 mmol) and K2CO3 (1.23 g, 8.94 mmol) were added, and the mixture was stirred at 80° C. for 3 hours. The reaction was quenched with water, and the product was extracted with EtOAc. The organic phase was washed with water (3×), then dried over Na2SO4 and evaporated under vacuum to yield 1.5 g of crude.

Workup

  1. customThe reaction was quenched with water
  2. extractionthe product was extracted with EtOAc
  3. washThe organic phase was washed with water (3×)
  4. dry with materialdried over Na2SO4
  5. customevaporated under vacuum
  6. customto yield 1.5 g of crude

Sources & evidence

ORD record
ord-ae8cf5bdbb064dc9b625280d514bc9c3
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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