Chloroacetyl chloride → Ammonia

HRID 2118042Notes

Reaction equation

HRID 2118042 reaction equation
C([N:3](CC)CC)C.[Cl:8][CH2:9][C:10](Cl)=[O:11].[Cl:13][C:14]1[CH:39]=[CH:38][C:17]2[N:18]3[C:22]([CH2:23][NH:24][CH2:25][C:16]=2[CH:15]=1)=[N:21][N:20]=[C:19]3[CH:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)[CH2:28][CH2:27]1>ClCCl>[NH3:3].[Cl:8][CH2:9][C:10]([N:24]1[CH2:23][C:22]2[N:18]([C:19]([CH:26]3[CH2:31][CH2:30][N:29]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=4)[CH2:28][CH2:27]3)=[N:20][N:21]=2)[C:17]2[CH:38]=[CH:39][C:14]([Cl:13])=[CH:15][C:16]=2[CH2:25]1)=[O:11]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chloride2×HCID 8471TriethylamineHCID 113264888-Chloro-1-(3,4,5,6-tetrahydro-2h-[1,2']bipyridinyl-4-yl)-5,6-dihydro4h-2,3,5,10b-tetraaza-benzo[e]azulene

Product 2

HCID 222AmmoniaHCID 21925637HCID 21925637, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.37 ml, 9.81 mmol) and chloroacetyl chloride (0.35 ml, 4.35 mmol) were added to a solution of the amine from example 4 (1.5 g, 3.95 mmol) in dichloromethane (50 ml), and the reaction stirred at room temperature for 2 hours. TLC analysis showed starting material remained, so additional chloroacetyl chloride (0.35 ml, 4.35 mmol) was added and the reaction was stirred for an additional 1.5 hours. The mixture was partitioned between dichloromethane and 2N sodium hydroxide solution and the layers separated. The aqueous phase was extracted with further dichloromethane and the combined organic solutions were washed with brine (50 ml), dried over magnesium sulphate, and evaporated under reduced pressure. The residual foam was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (95:5:0.5) to afford the title compound as a foam, 1.12 g.

Workup

  1. stirringthe reaction was stirred for an additional 1.5 hours
  2. customThe mixture was partitioned between dichloromethane and 2N sodium hydroxide solution
  3. customthe layers separated
  4. extractionThe aqueous phase was extracted with further dichloromethane
  5. washthe combined organic solutions were washed with brine (50 ml)
  6. dry with materialdried over magnesium sulphate
  7. customevaporated under reduced pressure
  8. customThe residual foam was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-22a1279137bc4a1d963230c5f9350068
Source dataset
uspto-grants-2008_10
Patent number
US07442795B2

Reaction notes

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