Triethylamine → Diisopropylether ethyl acetate

HRID 1862048Notes

Reaction equation

HRID 1862048 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]2[C:4]=1[CH2:5][CH2:6][CH:7]([C:16]([OH:18])=[O:17])[CH2:8]2.S(Cl)(Cl)=O.[NH2:23][C:24]1[CH:37]=[CH:36][C:27]([C:28]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[O:29])=[CH:26][CH:25]=1.[CH2:38](N([CH2:43][CH3:44])CC)[CH3:39]>CN(C)C=O.C(Cl)Cl.O.C1(C)C=CC=CC=1>[CH:3]([O:2][CH:43]([CH3:44])[CH3:24])([CH3:12])[CH3:4].[C:16]([O:18][CH2:38][CH3:39])(=[O:17])[CH3:7].[O:33]1[CH2:32][CH2:31][N:30]([C:28]([C:27]2[CH:36]=[CH:37][C:24]([NH:23][C:16]([CH:7]3[CH2:6][CH2:5][C:4]4[C:9](=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:3]=4[O:2][CH3:1])[CH2:8]3)=[O:18])=[CH:25][CH:26]=2)=[O:29])[CH2:35][CH2:34]1

Participants

10

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 5778154-(Morpholine-4-carbonyl)anilineHCID 186225095-Methoxy-8-nitro-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

Product 2

HCID 18622500N-(4-Morpholinocarbonylphenyl)-5-methoxy-8-nitro-1,2,3,4-tetrahydronaphthalene-2-carboxamideHCID 22281796Diisopropylether ethyl acetateYield 315.3%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-methoxy-8-nitro-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (1.0 g, 4 mmol), toluene (20 mL), N,N-dimethylformamide (10 drops) and thionyl chloride (1.5 mL, 20 mmol) was heated at 60° C. for 1 h. The solvents were removed in vacuo and the residue, dissolved in methylene chloride (20 mL), was added to a solution of 4-aminobenzoylmorpholine (820 m, 4 mmol, described in: Devlin J. P. J. Chem. Soc. Perkin Trans I, 1975, 830-841) and triethylamine (800 mg, 8 mmol) in methylene chloride (30 mL) at 5° C. After stirring at 20° C. for 2 h, water was added and the organic phase was separated, dried and the solvent removed in vacuo. The oily residue was crystallized from diisopropyl ether/ethyl acetate affording 1.2 g (73% yield) of the title compound as crystals: mp 186-189° C.; EIMS (70 eV) m/z (relative intensity) 439 (20, M+).

Workup

  1. customThe solvents were removed in vacuo
  2. dissolutionthe residue, dissolved in methylene chloride (20 mL)
  3. customthe organic phase was separated
  4. customdried
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-b9c659013cac4ad884bf99821ccf74e9
Source dataset
uspto-grants-2003_03
Patent number
US06534652B2

Reaction notes

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