Dimethylformamide → HCID 58034346, compound

HRID 1914830Notes

Reaction equation

HRID 1914830 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[N:13]=[CH:12][C:11]3[C:6](=[N:7][C:8](O)=[C:9]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[N:10]=3)[N:5]2[N:21]=1.CN(C=O)C.O=S(Cl)[Cl:29]>C(Cl)(Cl)Cl>[Cl:29][C:8]1[N:7]=[C:6]2[C:11]([CH:12]=[N:13][C:4]3[N:5]2[N:21]=[C:2]([CH3:1])[CH:3]=3)=[N:10][C:9]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178422280HCID 178422280, compound

Product 1

HCID 58034346HCID 58034346, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

A 40 mL scintillation vial containing Compound (10-4) (220 mg, 0.8 mmol, 1 eq.), CHCl3 (12 mL), DMF (12 mg, 0.16 mmol, 2 eq.), and SOCl2 (0.56 g, 3.2 mmol, 4 eq.) was heated at 70° C. under nitrogen for 1.5 hours. Then the mixture was allowed to cool and the solvent was removed in vacuo. The residue was dissolved in CHCl3 (20 mL) and washed with saturated NaHCO3 (5 mL). The water solution was extracted with CHCl3 (2×5 mL). The combined organic phases were dried over MgSO4. After filtration and concentration, the residue was purified by silica gel chromatography using EtOAc and heptane as the mobile phases to furnish Compound (10-5) as a yellowish solid.

Workup

  1. temperatureto cool
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in CHCl3 (20 mL)
  4. washwashed with saturated NaHCO3 (5 mL)
  5. extractionThe water solution was extracted with CHCl3 (2×5 mL)
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. filtrationAfter filtration and concentration
  8. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-bb8fd313a8034d108d95046f2f6c4db0
Source dataset
uspto-grants-2013_12
Patent number
US08614221B2

Reaction notes

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