Methylamine → HCID 178482479, compound

HRID 128757Notes

Reaction equation

HRID 128757 reaction equation
[CH3:1][C:2]1[CH:17]=[C:16]([C:18]2[N:22]=[C:21](C(Cl)(Cl)Cl)[O:20][N:19]=2)[CH:15]=[C:14]([CH3:27])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]1[O:12][N:11]=[C:10]([CH3:13])[CH:9]=1.[CH3:28][NH2:29]>CN(C)C=O.O>[CH3:1][C:2]1[CH:17]=[C:16]([C:18]2[NH:22][C:21](=[N:29][CH3:28])[O:20][N:19]=2)[CH:15]=[C:14]([CH3:27])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]1[O:12][N:11]=[C:10]([CH3:13])[CH:9]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 9845603HCID 9845603, compound

Product 1

HCID 178482479HCID 178482479, compoundYield 37.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The product of Example 12 (1.00 g, 2.32 mmol) was added to 5 ml of 40% aqueous methylamine in dimethylformamide (3-5 mL) and the mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (3x). The combined organic extracts were washed with water, brine, dried (MgSO4) and concentrated in vacuo. The crude residue (0.54 g) was purified by chromatography (Silica Gel 60, first with 2% methanol in methylene chloride and then with 50% ethyl acetate in hexanes) to give 300 mg (37.5%) of pure title compound as a yellow solid, mp 126.5°-127° C. (ethanol).

Workup

  1. extractionextracted with ethyl acetate (3x)
  2. washThe combined organic extracts were washed with water, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude residue (0.54 g) was purified by chromatography (Silica Gel 60

Sources & evidence

ORD record
ord-c26a479770aa44dd9e30a4b453cfd340
Source dataset
uspto-grants-1995_11
Patent number
US05464848

Reaction notes

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