Dimethylformamide → HCID 87879176, compound

HRID 989431Notes

Reaction equation

HRID 989431 reaction equation
S(Cl)([Cl:3])=O.CN(C=O)C.[C:10]([O:18][CH2:19][C@:20]12[C@@H:26]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C@@H:23]([O:24][CH2:25]1)[C@H:22]([N:35]1[CH:43]=[N:42][C:41]3[C:40](=O)[NH:39][CH:38]=[N:37][C:36]1=3)[O:21]2)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>ClCCl.C(OCC)(=O)C>[C:10]([O:18][CH2:19][C@:20]12[C@@H:26]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C@@H:23]([O:24][CH2:25]1)[C@H:22]([N:35]1[CH:43]=[N:42][C:41]3[C:36]1=[N:37][CH:38]=[N:39][C:40]=3[Cl:3])[O:21]2)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 137178931HCID 137178931, compound

Product 1

HCID 87879176HCID 87879176, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
30 °C

Procedure

Thionyl chloride (2.1 mL, 29 mmol) and DMF (1 mL) were added to a solution of compound 22 (1.24 g, 2.62 mmol) in dichloromethane. The mixture was stirred at 30° C. (oil bath) overnight, diluted with ethyl acetate (50 mL), washed with NaHCO3 (sat. aq., 100 mL) and water (2×50 mL), dried (Na2SO4), and concentrated under reduced pressure. A white solid residue was purified by column silica gel chromatography using 0 to 2% of methanol/dichloromethane as eluent. Yield: 1.2 g (93%) of compound 26 as a white solid material.

Workup

  1. washwashed with NaHCO3 (sat. aq., 100 mL) and water (2×50 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customA white solid residue was purified by column silica gel chromatography

Sources & evidence

ORD record
ord-24c059a35fc24343bb9ae601598ef0f1
Source dataset
uspto-grants-2003_10
Patent number
US06639059B1

Reaction notes

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