Triethylamine → N-[2-methyl-5-(3-morpholinobenzamido)phenyl]thiophene-2-carboxamide

HRID 2302250Notes

Reaction equation

HRID 2302250 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[NH2:9][C:10]1[CH:11]=[C:12]([NH:17][C:18](=[O:31])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[CH:20]=2)[CH:13]=[CH:14][C:15]=1[CH3:16].C(N(CC)CC)C>C(Cl)Cl>[CH3:16][C:15]1[CH:14]=[CH:13][C:12]([NH:17][C:18](=[O:31])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N:25]3[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)[CH:20]=2)=[CH:11][C:10]=1[NH:9][C:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 789282-Thiophenecarbonyl chlorideHCID 11301391N-(3-amino-4-methylphenyl)-3-morpholinobenzamide

Product 1

HCID 11327642N-[2-methyl-5-(3-morpholinobenzamido)phenyl]thiophene-2-carboxamideYield 33.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thiophene-2-carbonyl chloride (0.069 g) was added to a stirred suspension of N-(3-amino-4-methylphenyl)-3-morpholinobenzamide (0.104 g), triethylamine (0.15 ml) and methylene chloride (20 ml) and the resultant mixture was stirred at ambient temperature for 4 hours. The organic phase was washed with water and with a saturated aqueous sodium bicarbonate solution, dried (MgSO4) and evaporated. The residue was dissolved in methylene chloride (2 ml) and diethyl ether (20 ml) was added to give a precipitate which was isolated by filtration, washed with diethyl ether and dried. There was thus obtained the title compound (0.047 g); NMR Spectrum: (DMSOd6) 2.18 (t, 3H), 3.18 (t, 4H), 3.76 (t, 4H), 7.14 (d, 1H), 7.20 (m, 2H), 7.38 (m, 2H), 7.41 (s, 1H), 7.58 (m, 1H), 7.78 (s, 1H), 7.82 (d, 1H), 7.98 (d, 1H), 9.93 (s, 1H), 10.13 (s, 1H); Mass Spectrum: M+H+ 422.

Workup

  1. washThe organic phase was washed with water and with a saturated aqueous sodium bicarbonate solution
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. dissolutionThe residue was dissolved in methylene chloride (2 ml)
  5. additiondiethyl ether (20 ml) was added
  6. customto give a precipitate which
  7. customwas isolated by filtration
  8. washwashed with diethyl ether
  9. customdried

Sources & evidence

ORD record
ord-81f90d0aa9664327b48c9550eb4ff15c
Source dataset
uspto-grants-2002_08
Patent number
US06432949B1

Reaction notes

Loading…