Dimethylformamide → HCID 86621080, compound

HRID 900756Notes

Reaction equation

HRID 900756 reaction equation
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[N:9]=[C:10]([CH3:37])[N:11]([CH2:14][C:15]2[S:30][C:18]3[N:19]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:20](=[O:25])[N:21]([CH3:24])[C:22](=[O:23])[C:17]=3[C:16]=2[C:31]([N:33]([O:35]C)[CH3:34])=[O:32])[C:12]=1[Cl:13].CN(C)C=O>ClCCl>[Cl:7][C:8]1[N:9]=[C:10]([CH3:37])[N:11]([CH2:14][C:15]2[S:30][C:18]3[N:19]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:20](=[O:25])[N:21]([CH3:24])[C:22](=[O:23])[C:17]=3[C:16]=2[C:31]([N:33]([OH:35])[CH3:34])=[O:32])[C:12]=1[Cl:13]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 10184774HCID 10184774, compound

Product 1

HCID 86621080HCID 86621080, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.1 62 ml) was added to a stirred solution of the product of example 1 part d) (415 mg) and dimethylformamide (0.01 ml) in dichloromethane (4 ml). After 1 h the solution was evaporated under reduced pressure. The residue was dissolved in anhydrous tetrahydrofuran (3 ml) and 1 ml of the solution was added to a stirred solution of N-methylhydroxylamine hydrochloride (129 mg) in saturated aqueous sodium bicarbonate solution (2 ml). After 1 h, the mixture was diluted with water (10 ml) and extracted with ethyl acetate (3×10 ml). Organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure to give the sub-title compound (129 mg).

Workup

  1. customAfter 1 h the solution was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in anhydrous tetrahydrofuran (3 ml)
  3. addition1 ml of the solution was added to a stirred solution of N-methylhydroxylamine hydrochloride (129 mg) in saturated aqueous sodium bicarbonate solution (2 ml)
  4. additionthe mixture was diluted with water (10 ml)
  5. extractionextracted with ethyl acetate (3×10 ml)
  6. dry with materialOrganic extracts were dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b79732dfab45459dbeab391ea5900b67
Source dataset
uspto-grants-2008_04
Patent number
US07361660B2

Reaction notes

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