Dimethylamine → 1206456-47-4

HRID 1468202Notes

Reaction equation

HRID 1468202 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][C:18]([OH:20])=O)=[CH:16][C:3]1=2.[CH3:21][N:22](C=O)[CH3:23].S(Cl)(Cl)=O.N(C)C>C(#N)C>[CH3:21][N:22]([CH3:23])[C:18](=[O:20])[CH2:17][C:15]1[CH:14]=[CH:13][C:4]2[O:5][CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:2](=[O:1])[C:3]=2[CH:16]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 41448Isoxepac

Product 1

HCID 212691321206456-47-4Yield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
2.5 °C

Procedure

8 g (0.029 moles) of 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-acetic acid were dissolved in 30 ml of acetonitrile and 0.15 ml of DMF were added to this solution. 2.3 ml (0.032 moles) of thionyl chloride were added to the resulting solution at 20-25° C. Once the reaction had ended, the reaction mixture is slowly poured over an aqueous solution of 40% Me2NH (14.4 g, 0.32 ml) cooled at 0-5° C. and stirring was maintained at this temperature for 30 minutes. Subsequently, the organic part was distilled under reduced pressure and 80 ml of methylene chloride were added. The phases were decanted, separating the organic phase. The solvent was distilled, obtaining an oil with the product of the title with a yield of 60%.

Workup

  1. temperaturewas maintained at this temperature for 30 minutes
  2. distillationSubsequently, the organic part was distilled under reduced pressure and 80 ml of methylene chloride
  3. additionwere added
  4. customThe phases were decanted
  5. customseparating the organic phase
  6. distillationThe solvent was distilled
  7. customobtaining an oil with the product of the title with a yield of 60%

Sources & evidence

ORD record
ord-3d0c4d9ea43446f9a2c6794cf37cb484
Source dataset
uspto-grants-2015_04
Patent number
US09000195B2

Reaction notes

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