4-Methylmorpholine → HCID 178497991, compound

HRID 2053774Notes

Reaction equation

HRID 2053774 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:5]([OH:7])=O.C(N(CC)CC)C.CN1CCOCC1.[Cl:29][C:30]1[CH:40]=[CH:39][C:33]2[NH:34][C:35]([CH2:37][NH2:38])=[N:36][C:32]=2[CH:31]=1>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:5]([NH:38][CH2:37][C:35]1[NH:34][C:33]2[CH:39]=[CH:40][C:30]([Cl:29])=[CH:31][C:32]=2[N:36]=1)=[O:7]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 8471TriethylamineHCID 143722353-Chloro-4-(methoxycarbonyl)benzoic acidHCID 178510549HCID 178510549, compound

Product 1

HCID 178497991HCID 178497991, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.61 g (7.50 mmol) of 3-chloro-4-methoxycarbonylbenzoic acid is dissolved in 40 mL of N,N-dimethylformamide and combined with 1.30 g (8.00 mmol) of N,N′-carbonyldiimidazole and stirred for 15 minutes at ambient temperature under a nitrogen atmosphere. Then 1.0 mL (7.5 mmol) of triethylamine, 1.5 mL (15 mmol) of N-methylmorpholine, and 1.69 g (7.75 mmol) of C-(5-chloro-1H-benzimidazol-2-yl)methylamine are added successively and stirred for a further 16 hours at ambient temperature under a nitrogen atmosphere. Then the reaction mixture is poured into 1 L of ice water, the precipitate is separated off by filtering, washed with a little demineralized water, and dried at 40° C. Finally the product is recrystallized from petroleum ether/ethyl acetate (2:1). Yield: 2.40 g (85%); Rf value: 0.58 (silica gel; dichloromethane/ethanol=9:1); C17H13Cl2N3O3 (378.22); mass spectrum: (M−H)−=376/78/80 (chlorine isotope).

Workup

  1. stirringstirred for a further 16 hours at ambient temperature under a nitrogen atmosphere
  2. customthe precipitate is separated off
  3. filtrationby filtering
  4. washwashed with a little demineralized water
  5. customdried at 40° C
  6. customFinally the product is recrystallized from petroleum ether/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-b3bd13965b5e494481db3dbc4da7dbb5
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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