Triethylamine → HCID 86679462, compound

HRID 1776511Notes

Reaction equation

HRID 1776511 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[NH2:6].C(N([CH2:17][CH3:18])CC)C.Cl[S:20]([CH2:23][C:24]([O:26]C)=[O:25])(=[O:22])=[O:21]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:6][S:20]([CH2:23][C:24]([O:26][CH2:17][CH3:18])=[O:25])(=[O:22])=[O:21])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 227703,4-DimethoxyanilineHCID 11435213Methyl (chlorosulfonyl)acetate

Product 1

HCID 86679462HCID 86679462, compoundYield 109.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3,4-dimethoxyaniline (0.740 g, 4.83 mmol) and triethylamine (0.587 g, 5.80 mmol) in dry DCM (10 ml), a solution of methyl 2-(chlorosulfonyl)acetate (1 g, 5.36 mmol) in dry DCM (5 ml) was added dropwise at RT. The mixture was stirred for 2 hours, then the solvent was removed under vacuum; the residue was dissolved in EtOAc, washed with HCl 1N, NaHCO3 sat. sol, and brine, dried over Na2SO4, filtered and evaporated to give 1.6 g of a dark oil. After trituration with iPrOH (8 ml) and filtration, the desired product was obtained (0.74 g, 2.440 mmol, 50.5% yield, MS/ESI+ 311.9 [MNa]+) and used in the next step without further purification.

Workup

  1. customthe solvent was removed under vacuum
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with HCl 1N, NaHCO3 sat. sol, and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-2eb71174afce4355aa8709b6c4b32361
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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