Hydrochloric Acid → HCID 21224857, compound

HRID 2394388Notes

Reaction equation

HRID 2394388 reaction equation
[Cl:1][C:2]1[C:3]([CH2:11][N:12]2[C:16](Br)=[C:15]([Br:18])[N:14]=[C:13]2[CH:19]2[O:23][CH2:22][CH2:21][O:20]2)=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.[O:24]1CCC[CH2:25]1.C([Mg]Br)C.Cl>CCOCC.C(OCC)(=O)C.CN(C)C=O>[Br:18][C:15]1[N:14]=[C:13]([CH:19]2[O:23][CH2:22][CH2:21][O:20]2)[N:12]([CH2:11][C:3]2[C:2]([Cl:1])=[CH:10][C:6]3[O:7][CH2:8][O:9][C:5]=3[CH:4]=2)[C:16]=1[CH:25]=[O:24]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 21224829HCID 21224829, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 21224857HCID 21224857, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

10 g of the product obtained in Stage A above is introduced into 200 ml of tetrahydrofuran and 10 ml of ethyl magnesium bromide in a 3M solution in ether is added dropwise. The reaction medium is maintained under agitation for 20 minutes at ambient temperature. 10 ml of dimethylformamide is then added to the reaction medium obtained and agitation is carried out for 2 hours at ambient temperature. The medium is hydrolyzed by the addition of 200 ml of dilute hydrochloric acid, extraction is carried out with ethyl acetate, followed by washing with water then drying and after impasting in isopropyl ether, 7.6 g of expected product is recovered, which is used as it is for the following stage.

Workup

  1. additionis added dropwise
  2. customobtained
  3. washby washing with water
  4. customthen drying
  5. custom7.6 g of expected product is recovered

Sources & evidence

ORD record
ord-918206d0ff2449c0870edaacd96d9467
Source dataset
uspto-grants-1998_09
Patent number
US05811444

Reaction notes

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