Diethyl Ether → HCID 8823780, compound

HRID 1987719Notes

Reaction equation

HRID 1987719 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): δ 1.31, 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-0d9a16edb2324945b659d453e34bc535
Source dataset
uspto-grants-2009_06
Patent number
US07553809B2

Reaction notes

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