Oxalyl chloride → HCID 15872077, compound

HRID 617134

Reaction equation

HRID 617134 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[C:7]12([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH2:8]1)[CH2:14]2>C1(C)C=CC=CC=1>[C:7]12([N:17]3[C:18]4[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:1](=[O:5])[C:2]3=[O:3])[CH2:8][CH:9]3[CH2:10][CH:11]([CH2:12][CH:13]([CH2:15]3)[CH2:14]1)[CH2:16]2

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 303939N-phenyladamantan-1-amine

Product 1

HCID 15872077HCID 15872077, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

Under a N2 atmosphere was added 1.97 g (15.6 mmol) of oxalyl chloride to 3 ml of dry toluene which was cooled to 0° C. To this solution was added 3.55 g (15.6 mmol) of N-1-adamantylaniline in toluene (8 ml). The reaction was allowed to stir for 30 min. at 0° C. and then heated at 65° C. for 3 hours. Additional solvent (10 ml) was added and the reaction was kept at 65° C. for 72 hours. The solvent was removed and the residue was allowed to stir at 160° C. for 5 hours. The crude reaction mixture was allowed to cool and was chromatographed on silica gel using 6:1 hexane:EtOAc to afford crude product, which was triturated with isopropyl ether (IPE) to generate 164 mg (4.4%) of 1-adamantylisatin combined with product contaminated with significant amounts of impurities.

Workup

  1. temperatureheated at 65° C. for 3 hours
  2. waitthe reaction was kept at 65° C. for 72 hours
  3. customThe solvent was removed
  4. stirringto stir at 160° C. for 5 hours
  5. customThe crude reaction mixture
  6. temperatureto cool
  7. customwas chromatographed on silica gel using 6:1 hexane
  8. customEtOAc to afford crude product, which
  9. customwas triturated with isopropyl ether (IPE)

Sources & evidence

ORD record
ord-6f5041cf505a4f4d9553c58973908c93
Source dataset
uspto-grants-1999_09
Patent number
US05948781

Linked notes

Loading…