Chloroacetyl chloride → Ammonia

HRID 1243588Notes

Reaction equation

HRID 1243588 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-ed153d2815884f9fad56c4088762b361
Source dataset
uspto-grants-2006_10
Patent number
US07119088B2

Reaction notes

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