Sodium Chloride → Ethyl 2-[(6-chloronaphthalen-2-ylsulfonyl)(2,2-diethoxyethyl)amino]acetate

HRID 1244790Notes

Reaction equation

HRID 1244790 reaction equation
[CH2:1]([O:3][CH:4]([O:13][CH2:14][CH3:15])[CH2:5][NH:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:2].C(N(CC)CC)C.[Cl:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[CH:30]=[C:29]([S:34](Cl)(=[O:36])=[O:35])[CH:28]=[CH:27]2.[Cl-].[Na+]>C(Cl)Cl>[Cl:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[CH:30]=[C:29]([S:34]([N:6]([CH2:5][CH:4]([O:3][CH2:1][CH3:2])[O:13][CH2:14][CH3:15])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:36])=[O:35])[CH:28]=[CH:27]2

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 106351296-Chloronaphthalene-2-sulfonyl chlorideHCID 11790686Ethyl 2-[(2,2-diethoxyethyl)amino]acetate

Product 1

HCID 11812307Ethyl 2-[(6-chloronaphthalen-2-ylsulfonyl)(2,2-diethoxyethyl)amino]acetateYield 73.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound obtained in Step 1 (504 mg) was suspended in methylene chloride (20 ml) and to the suspension were added triethylamine (336 ml) and then 6-chloronaphthalene-2-sulfonyl chloride (600 mg) under cooling with ice. After stirring the mixture overnight at room temperature, saturated sodium chloride solution was added and the mixture was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and thereafter the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=20:1–4:1) to obtain the title compound (750 mg).

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=20:1–4:1)

Sources & evidence

ORD record
ord-250da0f4600049208aeaaa79bda6e47c
Source dataset
uspto-grants-2006_10
Patent number
US07122662B2

Reaction notes

Loading…