Chloroform → HCID 58034346, compound

HRID 1914850Notes

Reaction equation

HRID 1914850 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.C(Cl)(Cl)[Cl:28]>>[Cl:28][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

4

Reactant 3

HCID 6212ChloroformHCID 6228DimethylformamideHCID 178422280HCID 178422280, compound

Product 1

HCID 58034346HCID 58034346, compound

Conditions

Temperature
70 °C

Procedure

A 40 mL scintillation vial containing Compound [CCXXX] (220 mg, 0.8 mmol, 1 eq.), CHCl3 (12 mL), DMF (12 mg, 0.16 mmol, 2 eq.), and SOCK (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 heptanes as the mobile phases to furnish Compound [CCXXXI] as a yellowish solid: LCMS (m/e) 296 (M+H); 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.57 (s, 3H) 6.71 (s, 1H) 7.46-7.52 (m, 3H) 7.79 (dd, J=6.61, 3.00 Hz, 2H) 9.02 (s, 1H).

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-53fe49a354ac4d62ab947679e01298b8
Source dataset
uspto-grants-2013_12
Patent number
US08614221B2

Reaction notes

Loading…