Hydrochloric Acid → HCID 22133001, compound

HRID 1856849Notes

Reaction equation

HRID 1856849 reaction equation
[Cl:1][C:2]1[C:3]([CH2:11][N:12]2[C:16]([Br:17])=[C:15]([Br:18])[N:14]=[C:13]2Br)=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.C(Cl)Cl.C([Mg]Br)C.Cl.[CH2:28]([O:30]CC)C>CN(C)C=O>[Br:18][C:15]1[N:14]=[C:13]([CH:28]=[O:30])[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[Br:17]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 6344DichloromethaneHCID 22133000HCID 22133000, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 22133001HCID 22133001, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

20 g of the product obtained in Stage 1 above is introduced into 200 ml of anhydrous methylene chloride to which 500 ml of anhydrous ethyl ether is added. A 3M solution of ethyl magnesium bromide in ethyl ether is added and the whole is left under agitation for 20 minutes at ambient temperature. Then an excess (15 ml) of anhydrous dimethylformamide is added. After 2 hours at ambient temperature, hydrolysis is carried out with 200 ml of 1N hydrochloric acid followed by extraction 3 times with 300 ml of ethyl acetate. The organic phase is washed with saturated sodium chloride then dried and evaporated to dryness. In this way 14.5 g of expected product is obtained.

Workup

  1. additionis added
  2. waitAfter 2 hours at ambient temperature
  3. customhydrolysis
  4. extractionfollowed by extraction 3 times with 300 ml of ethyl acetate
  5. washThe organic phase is washed with saturated sodium chloride
  6. customthen dried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-6fe4a1126c174c0893cdd44082f4ecc4
Source dataset
uspto-grants-2000_11
Patent number
US06143774

Reaction notes

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