1-Amino-3,3-diethoxypropane → HCID 67304186, compound

HRID 1008954Notes

Reaction equation

HRID 1008954 reaction equation
[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[CH2:5][CH2:6][NH2:7])[CH3:2].[CH3:11][C:12]1([CH3:29])[O:17][C:16](=[O:18])[C:15](=[C:19](SC)[NH:20][C:21]2[CH:25]=[CH:24][S:23][CH:22]=2)[C:14](=[O:28])[O:13]1>ClCCl.CO>[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[CH2:5][CH2:6][NH:7][C:19]([NH:20][C:21]1[CH:25]=[CH:24][S:23][CH:22]=1)=[C:15]1[C:14](=[O:28])[O:13][C:12]([CH3:29])([CH3:11])[O:17][C:16]1=[O:18])[CH3:2]

Participants

5

Reactant 2

HCID 5210291-Amino-3,3-diethoxypropaneHCID 59744970HCID 59744970, compound

Product 1

HCID 67304186HCID 67304186, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

3,3-Diethoxypropylamine (210.7 g, 1.43 mol) was added in portions to the solution of 2,2-dimethyl-5-(methylsulfanyl-thiophene-3-ylamino-methylene)-[1,3]dioxane-4,6-dione (407.3 g, 1.36 mol) in dichloromethane (1.7 L) and methanol (0.36 L) over 60 min, while the reaction temperature was kept under 25° C. with a water bath. After stirring for 1.5 h at room temperature, the reaction mixture was diluted with dichloromethane (0.8 L). The organic layer was separated and washed with aqueous ammonium chloride solution (400 mL, made of 200 mL of sat. NH4Cl and 200 mL of water), brine (300 mL) and dried over magnesium sulfate. Concentration of the reaction mixture under reduced pressure afforded a dark oil. Xylenes (500 ml) were added and the mixture concentrated under reduced pressure to give the intermediate 5-((3,3-Diethoxypropylamino)(thiophene-3-ylamino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione. The resultant dark oil was used directly in next step without further purification. 1H NMR (400 MHz, CDCl3) δ 1.65 (m, 6H), 1.73 (s, 6H), 1.78 (m, 2H), 2.98 (q, 2H, J=6.4 Hz), 3.45 (m, 2H), 3.60 (m, 2H), 4.50 (t, 1H, J=5.2 Hz), 6.98 (dd, 1H, J=1.6, 5.2 Hz), 7.05 (dd, 1H, J=1.2, 3.2 Hz), 7.33 (dd, 1H, J=3.2, 5.2 Hz), 10.2 (s, 1H), 11.3 (s, 1H).

Workup

  1. customwas kept under 25° C. with a water bath
  2. customThe organic layer was separated
  3. washwashed with aqueous ammonium chloride solution (400 mL, made of 200 mL of sat. NH4Cl and 200 mL of water), brine (300 mL)
  4. dry with materialdried over magnesium sulfate
  5. customConcentration of the reaction mixture under reduced pressure afforded a dark oil
  6. concentrationthe mixture concentrated under reduced pressure

Sources & evidence

ORD record
ord-260c71a93c934ce292b0f36bf06a778b
Source dataset
uspto-grants-2011_07
Patent number
US07973050B2

Reaction notes

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