Triethylamine → N-(2-diethylamino-ethyl)-4-(bismethanesulfonylamino)-2-methoxy-benzamide

HRID 2262353Notes

Reaction equation

HRID 2262353 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[O:7])=[C:4]([O:18][CH3:19])[CH:3]=1.C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:14]([N:11]([CH2:12][CH3:13])[CH2:10][CH2:9][NH:8][C:6](=[O:7])[C:5]1[CH:16]=[CH:17][C:2]([N:1]([S:28]([CH3:27])(=[O:30])=[O:29])[S:28]([CH3:27])(=[O:30])=[O:29])=[CH:3][C:4]=1[O:18][CH3:19])[CH3:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 773744-Amino-N-[2-(diethylamino)ethyl]-2-methoxybenzamideHCID 516892Sodium Bicarbonate

Product 1

HCID 66934940N-(2-diethylamino-ethyl)-4-(bismethanesulfonylamino)-2-methoxy-benzamideYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

265 mg (1 mmol) of 4-amino-N-(2-diethylamino-ethyl)-2-methoxy-benzamide is introduced into 15 ml of methylene chloride and mixed in succession with 111 mg (1.1 mmol) of triethylamine and 126 mg (1.1 mmol) of methanesulfonic acid chloride. It is stirred for 2 hours at room temperature and then allowed to stand overnight. It is then mixed with 25 ml of saturated sodium bicarbonate solution and shaken out three times with 25 ml each of methylene chloride. The collected organic phase is dried, filtered and concentrated by evaporation. The residue is chromatographed on 10 g of basic silica gel (Isolute flash Si NH2) with a gradient from cyclohexane:ethyl acetate=100:0 to 50:50. 232 mg (52.6% of theory) of N-(2-diethylamino-ethyl)-4-(bismethanesulfonylamino)-2-methoxy-benzamide with a melting point of 144.1° C. is obtained.

Workup

  1. waitto stand overnight
  2. customThe collected organic phase is dried
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed on 10 g of basic silica gel (Isolute flash Si NH2) with a gradient from cyclohexane

Sources & evidence

ORD record
ord-d7db9b057cd24ffa91942e1dcf43f602
Source dataset
uspto-grants-2010_12
Patent number
US07850948B2

Reaction notes

Loading…