Dichloromethane → HCID 18957909, compound

HRID 2379123Notes

Reaction equation

HRID 2379123 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N:15]3[C:19]4[CH:20]=[CH:21][C:22]([C:24]([F:27])([F:26])[F:25])=[CH:23][C:18]=4[N:17]=[CH:16]3)[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[C:28](OC(=O)C)(=[O:30])[CH3:29].C(Cl)Cl>O>[C:28]([NH:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N:15]3[C:19]4[CH:20]=[CH:21][C:22]([C:24]([F:27])([F:26])[F:25])=[CH:23][C:18]=4[N:17]=[CH:16]3)[CH:10]=2)[CH:6]=[CH:7][CH:8]=1)(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 21800743HCID 21800743, compound

Product 1

HCID 18957909HCID 18957909, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound 8a (0.7 g, 1.79 mmol) was converted to the corresponding free base by partitioning between 0.1M aqueous NaOH (200 ml) and diethyl ether (200 ml). The phases were separated and the aqueous phase was extracted twice with ether. The combined ethereal phases were dried and evaporated. The residue was dissolved in dry methylene chloride (20 ml). Acetic anhydride (0.22 g, 2.15 mmol) was slowly added with ice cooling. After completed addition the mixture was stirred for one hour at room temperature. Methylene chloride (50 ml) and water (50 ml) was added and the aqueous phase was separated. The organic phase was dried and evaporated and the crude product purified by column chromatography, first with methylene chloride, then with methylene chloride/methanol (19:1 ), as eluent. Yield 400 mg, mp 118°-120° C.

Workup

  1. customby partitioning between 0.1M aqueous NaOH (200 ml) and diethyl ether (200 ml)
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted twice with ether
  4. customThe combined ethereal phases were dried
  5. customevaporated
  6. dissolutionThe residue was dissolved in dry methylene chloride (20 ml)
  7. additionaddition the mixture
  8. customthe aqueous phase was separated
  9. customThe organic phase was dried
  10. customevaporated
  11. customthe crude product purified by column chromatography, first with methylene chloride

Sources & evidence

ORD record
ord-c660c6b7edd14e539d0559df5d5c2e77
Source dataset
uspto-grants-1994_11
Patent number
US05360809

Reaction notes

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