Chlorosuccinimide → HCID 13457727, compound

HRID 462761Notes

Reaction equation

HRID 462761 reaction equation
[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10]2[N:11]([CH:18]=[CH:19][CH:20]=2)[N:12]([CH3:17])[C:13](=[O:16])[CH2:14][N:15]=1.[Cl:21]N1C(=O)CCC1=O>O1CCCC1>[ClH:21].[Cl:1][C:18]1[N:11]2[N:12]([CH3:17])[C:13](=[O:16])[CH2:14][N:15]=[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[F:2])[C:10]2=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 13457725HCID 13457725, compound

Product 1

HCID 13457727HCID 13457727, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution containing 5-(2-fluorophenyl)-1-methyl-1H-pyrrolo[1,2-b][1,2,5]triazepin-2(3H)-one hydrochloride (3.3 g, 12.9 mmol) and N-chlorosuccinimide (1.87 g, 14 mmol) in 100 ml of dry tetrahydrofuran was refluxed under N2 for 3 hours. The resultant solution was evaporated and the residual oil was taken up in 200 ml of EtOAc, washed with H2O, dried (MgSO4), filtered, and evaporated to an oil. This oil was purified by flash chromatography (silica, 4:7 hexane-ether) to given an oil (2.1 g). This oil was treated with ethereal HCl and the resultant solid was recrystallized from isopropanol-ether to give 2.36 g (55%) of powder, m.p. 218° dec.

Workup

  1. temperaturewas refluxed under N2 for 3 hours
  2. customThe resultant solution was evaporated
  3. washwashed with H2O
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to an oil
  7. customThis oil was purified by flash chromatography (silica, 4:7 hexane-ether)
  8. additionThis oil was treated with ethereal HCl
  9. customthe resultant solid was recrystallized from isopropanol-ether

Sources & evidence

ORD record
ord-e2dc9bd7c9af44659fc1b7b4ee933eb0
Source dataset
uspto-grants-1985_05
Patent number
US04517195

Reaction notes

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