Triethylamine → HCID 54191610, compound

HRID 1155277Notes

Reaction equation

HRID 1155277 reaction equation
[CH2:1]([N:3]([CH2:6][CH2:7][NH:8][C:9](=[O:24])[C:10]1[CH:15]=[C:14]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:13]([Cl:21])=[CH:12][C:11]=1[O:22][CH3:23])[CH2:4]C)C.C(N(CC)CC)C.[CH3:32][N:33]([CH3:38])[S:34](Cl)(=[O:36])=[O:35].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:1][N:3]([CH2:6][CH2:7][NH:8][C:9](=[O:24])[C:10]1[CH:15]=[C:14]([N:16]([S:34]([N:33]([CH3:38])[CH3:32])(=[O:36])=[O:35])[S:17]([CH3:20])(=[O:19])=[O:18])[C:13]([Cl:21])=[CH:12][C:11]=1[O:22][CH3:23])[CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 516892Sodium BicarbonateHCID 12790642HCID 12790642, compound

Product 1

HCID 54191610HCID 54191610, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(diethylaminoethyl)-4-chloro-5-methanesulfonamido-2-methoxybenzamide (570 mg), triethylamine (914 mg) and N,N-dimethylsulfamoyl chloride (1.3 g) in methylene chloride (30 ml) is refluxed for 40 hours. The reaction mixture is mixed with aqueous sodium hydrogen-carbonate. The organic layer is separated, washed with water, dried over anhydrous sodium sulfate and concentrated. The intermediary N-(dimethylaminoethyl)-4-chloro-5-[N-(dimethylaminosulfonyl)-methanesulfonamido]-2-methoxybenzamide obtained as a residue is mixed with 10% aqueous sodium hydroxide (10 ml) and methanol (10 ml) and refluxed for 10 minutes. The reaction mixture is concentrated to remove methanol and the residue is once acidified with 6N hydrochloric acid, neutralized with aqueous sodium hydrogen-carbonate, salted out with brine, and shaken with methylene chloride. The organic layer is dried over anhydrous sodium sulfate and the methylene chloride is evaporated. The residue is chromatographed on a column of alumina, which is eluted with methylene chloride to 1% methanol/methylene chloride. The eluate is concentrated and the residue is washed with ethyl acetate-isopropyl ether to give N-(diethylaminoethyl) -4-chloro-5-(N-dimethylaminosulfonyl)amino-2-methoxybenzamide (410 mg) as crystals melting at 110° to 110.5° C.

Workup

  1. customThe organic layer is separated
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7e85e1c032944f3a9db45dcb9c06e174
Source dataset
uspto-grants-1981_11
Patent number
US04301159

Reaction notes

Loading…