Dimethylformamide → HCID 21224857, compound

HRID 1856851Notes

Reaction equation

HRID 1856851 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH:19]2[O:23][CH2:22][CH2:21][O:20]2)[N:5]([CH2:8][C:9]2[C:17]([Cl:18])=[CH:16][C:12]3[O:13][CH2:14][O:15][C:11]=3[CH:10]=2)[C:6]=1Br.[O:24]1CCC[CH2:25]1.C([Mg]Br)C.CN(C)C=O>C(OC(C)C)(C)C>[Br:1][C:2]1[N:3]=[C:4]([CH:19]2[O:23][CH2:22][CH2:21][O:20]2)[N:5]([CH2:8][C:9]2[C:17]([Cl:18])=[CH:16][C:12]3[O:13][CH2:14][O:15][C:11]=3[CH:10]=2)[C:6]=1[CH:25]=[O:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 21224829HCID 21224829, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 21224857HCID 21224857, compound

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

10 g of the product obtained in Stage 3 above is introduced into 200 ml of anhydrous tetrahydrofuran. 10 ml of ethyl magnesium bromide (3M solution in ethyl ether) is added and the reaction medium is left under agitation for 20 minutes at ambient temperature. Then an excess of anhydrous dimethylformamide is added. After 2 hours at ambient temperature, hydrolysis is carried out with 200 ml of 1N hydrochloric acid and extraction is carried out 3 times with 300 ml of ethyl acetate. The organic phase is washed with saturated sodium chloride then dried and evaporated to dryness. The residue obtained is impasted in isopropyl ether. In this way 7.6 g of expected product is obtained, which is used without purification for the following stage.

Workup

  1. waitAfter 2 hours at ambient temperature
  2. customhydrolysis
  3. extractionis carried out with 200 ml of 1N hydrochloric acid and extraction
  4. washThe organic phase is washed with saturated sodium chloride
  5. customthen dried
  6. customevaporated to dryness
  7. customThe residue obtained

Sources & evidence

ORD record
ord-2c6c6d3b3e4c440883187f8c521b9b73
Source dataset
uspto-grants-2000_11
Patent number
US06143774

Reaction notes

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