Triethylamine → HCID 12790641, compound

HRID 1155276Notes

Reaction equation

HRID 1155276 reaction equation
[CH2:1]([N:3]([CH2:6][CH2:7][NH:8][C:9](=[O:20])[C:10]1[CH:15]=[C:14]([NH2:16])[C:13]([Cl:17])=[CH:12][C:11]=1[O:18][CH3:19])[CH2:4][CH3:5])[CH3:2].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:1]([N:3]([CH2:6][CH2:7][NH:8][C:9](=[O:20])[C:10]1[CH:15]=[C:14]([N:16]([S:29]([CH3:28])(=[O:31])=[O:30])[S:29]([CH3:28])(=[O:31])=[O:30])[C:13]([Cl:17])=[CH:12][C:11]=1[O:18][CH3:19])[CH2:4][CH3:5])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 12790640HCID 12790640, compound

Product 1

HCID 12790641HCID 12790641, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-(diethylaminoethyl)-5-amino 4-chloro-2-methoxybenzamide (1.1 g) and triethylamine (815 mg) in dry methylene chloride (11 ml) is added dropwise a solution of methanesulfonyl chloride (882 mg) in dry methylene chloride (5ml) under ice-cooling and stirring and the resultant mixture is stirred at room temperature for 30 minutes. The reaction mixture is mixed with aqueous sodium hydrogen-carbonate and the methylene chloride layer is separated. The organic layer is washed with water, dried over anhydrous sodium sulfate and concentrated. The intermediary N-(diethylaminoethyl)-5-bis(methanesulfonyl)amino-4-chloro-2-methoxybenzamide obtained as a residue is mixed with 10 % aqueous sodium hydroxide (18ml) and methanol (2 ml) and heated at 50° C. for 30 minutes. The reaction mixture is acidified with conc. hydrochloric acid, neutralized with aqueous sodium hydrogencarbonate, salted out with brine, and shaken with methylene chloride. The organic layer is dried over anhydrous sodium sulfate, and concentrated. The residue is chromatographed on a column of alumina, which is eluted with methylene chloride. The eluate is concentrated and the residue is washed with ethyl acetate - isoproyl ether to give N-(diethylaminoethyl)-4-chloro-5-methanesulfonamido-2-methoxybenzamide (993 mg) as crystals melting at 123° to 123.5° C.

Workup

  1. temperaturecooling
  2. customthe methylene chloride layer is separated
  3. washThe organic layer is washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9b70d2da0709419f90f94b605cfd5287
Source dataset
uspto-grants-1981_11
Patent number
US04301159

Reaction notes

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