Chloroform → HCID 178463596, compound

HRID 2227344Notes

Reaction equation

HRID 2227344 reaction equation
[CH:1]1([C:4]2[NH:12][C:11]3[C:10]([NH:13][CH2:14][CH3:15])=[N:9][C:8](=S)[N:7]([CH2:17][CH3:18])[C:6]=3[N:5]=2)[CH2:3][CH2:2]1.C(Cl)(Cl)Cl.C(OC(C)C)(C)C>[OH-].[Na+].[Ni]>[CH:1]1([C:4]2[N:5]=[C:6]3[C:11]([N:12]=2)=[C:10]([NH:13][CH2:14][CH3:15])[N:9]=[CH:8][N:7]3[CH2:17][CH3:18])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6212ChloroformHCID 7914Diisopropyl EtherHCID 15541455HCID 15541455, compound

Product 1

HCID 178463596HCID 178463596, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 14798Sodium HydroxideSolvent2×

Conditions

Temperature
67.5 °C

Procedure

The product of step (i) (11.85 g) was dissolved in 2N NaOH (270 ml) and 10N NaOH (27 ml) and heated to 65° C. Within 1.25 hours 50% Ni—Al alloy (518 mmoles of Ni and 1125 mmoles of Al) (60.8 g) was added under vigorous stirring at 65-70° C. After a further 0.75 hr at the same temperature the reaction mixture was cooled to room temperature and treated with chloroform (400 ml). The nickel was filtered off and washed with 350 ml of chloroform and 150 ml of water. The filtrate was separated and the chloroform layer evaporated to dryness. The residue (19.64 g) was dissolved in acetone (100 ml), treated with 2 portions of charcoal (0.15 g) filtered, and evaporated. The residue was treated with diethylether (100 ml) and crystals collected (6.10 g), mp 80-96° C. A second crop gave 1.25 g. A recrystallized sample from diisopropylether had mp 103-105° C.

Workup

  1. temperatureAfter a further 0.75 hr at the same temperature the reaction mixture was cooled to room temperature
  2. filtrationThe nickel was filtered off
  3. washwashed with 350 ml of chloroform and 150 ml of water
  4. customThe filtrate was separated
  5. customthe chloroform layer evaporated to dryness
  6. dissolutionThe residue (19.64 g) was dissolved in acetone (100 ml)
  7. additiontreated with 2 portions of charcoal (0.15 g)
  8. filtrationfiltered
  9. customevaporated
  10. additionThe residue was treated with diethylether (100 ml) and crystals
  11. customcollected (6.10 g), mp 80-96° C
  12. customA second crop gave 1.25 g

Sources & evidence

ORD record
ord-af7b13654f4849c2bd249faa057515fe
Source dataset
uspto-grants-2002_07
Patent number
US06413975B1

Reaction notes

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