Diethyl Ether → HCID 8823780, compound

HRID 277299Notes

Reaction equation

HRID 277299 reaction equation
Cl[S:2]([C:5]1[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:4])=[O:3].[NH2:15][C:16]1[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20].C(N(CC)CC)C.C(OCC)C>C(Cl)Cl>[C:19]([C:18]1[CH:17]=[C:16]([NH:15][S:2]([C:5]2[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=2[C:7]([O:9][CH3:10])=[O:8])(=[O:4])=[O:3])[CH:26]=[CH:25][CH:24]=1)([O:21][CH2:22][CH3:23])=[O:20]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 11400Ethyl 3-aminobenzoateHCID 117830Benzoic acid, 2-(chlorosulfonyl)-, methyl ester

Product 1

HCID 8823780HCID 8823780, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl 2-(chlorosulfonyl)-benzoate (2.25 g, 8.73 mmol) in methylene chloride (20 mL) was added dropwise to a solution of ethyl 3-aminobenzoate (1.44 g, 8.73 mmol) and triethylamine (1.21 mL, 8.73 mmol) in methylene chloride (10 mL) at 0° C. The reaction was allowed to warm to room temperature and stirred overnight. The reaction mixture was washed with water (20 mL), aqueous HCl (1 M, 20 mL) and aqueous NaOH (1 M, 20 mL), dried (MgSO4—, filtered and concentrated in vacuo to give an orange oil. Trituration with ethyl ether gave N-(3′-carboethoxyphenyl)-2-(carbomethoxy)benzenesulfonamide as white solid. 1H NMR (200 MHz, CDCl3): δ1.31, t, J=6.0 Hz, 3H; 4.00, s, 3H; 4.29, q, J=6.0 Hz, 2H; 7.23-7.61, m, 5H; 7.66-7.92, m, 3H; 8.26, br s , 1H.

Workup

  1. washThe reaction mixture was washed with water (20 mL), aqueous HCl (1 M, 20 mL) and aqueous NaOH (1 M, 20 mL)
  2. dry with materialdried (MgSO4—
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give an orange oil

Sources & evidence

ORD record
ord-1aaa9066a7924b1787c26b38dc54f0b8
Source dataset
uspto-grants-2002_03
Patent number
US06355683B1

Reaction notes

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