Hydrochloric Acid → HCID 21483902, compound

HRID 1415214Notes

Reaction equation

HRID 1415214 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][C:16](O)=[O:17])=[C:9]([Cl:13])[C:10]=2[Cl:12])[CH2:5][CH2:4][CH:3]1[CH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1.S(Cl)(Cl)=O.Cl.[CH2:29]([NH:31][CH2:32][CH3:33])[CH3:30]>C1C=CC=CC=1>[CH2:29]([N:31]([CH2:32][CH3:33])[C:16](=[O:17])[CH2:15][O:14][C:8]1[CH:7]=[C:6]2[C:11](=[C:10]([Cl:12])[C:9]=1[Cl:13])[C:2](=[O:1])[CH:3]([CH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[CH2:4][CH2:5]2)[CH3:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8021DiethylamineHCID 24386Thionyl ChlorideHCID 21483949HCID 21483949, compound

Product 1

HCID 21483902HCID 21483902, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The product of Example I, Step 5 (4.0 g., 0.02 mole) is added to thionyl chloride (11 g.) and the mixture is refluxed until HCl and SO2 are no longer evolved (about 1 hour). The excess thionyl chloride is evaporated. The residue is dissolved in benzene and a solution of diethylamine (3.6 g., 0.05 mole) in benzene is added. The mixture is kept for 1 hour and then evaporated to dryness. The residue is washed with water, 10% sodium bicarbonate and with water and airdried to obtain N,N-diethyl-(1-oxo-2-cyclopentyl-7,8-dichloro-1,2,3,4-tetrahydro-6-naphthyloxy)acetamide.

Workup

  1. custom(about 1 hour)
  2. customThe excess thionyl chloride is evaporated
  3. dissolutionThe residue is dissolved in benzene
  4. customevaporated to dryness
  5. washThe residue is washed with water, 10% sodium bicarbonate and with water

Sources & evidence

ORD record
ord-32be3b1710324ebbaf4e18140ca2c4e0
Source dataset
uspto-grants-1977_01
Patent number
US04003927

Reaction notes

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