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Chloroacetyl chloride → HCID 53833167, compound

HRID 893020
Notes
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Reaction equation

HRID 893020 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[C:5]([CH3:10])[C:4]=1[OH:11].Cl[CH2:13][C:14](Cl)=[O:15].[N:17]1([C:22]2[N:27]=[C:26]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[CH:25]=[C:24]([N:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)[N:23]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.C(#N)C.C(N(CC)CC)C>[N:17]1([C:22]2[N:27]=[C:26]([N:28]3[CH2:33][CH2:32][N:31]([CH2:13][C:14]([NH:9][C:7]4[CH:8]=[C:3]([CH3:2])[C:4]([OH:11])=[C:5]([CH3:10])[CH:6]=4)=[O:15])[CH2:30][CH2:29]3)[CH:25]=[C:24]([N:34]3[CH2:35][CH2:36][CH2:37][CH2:38]3)[N:23]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 82667Phenol, 4-amino-2,6-dimethyl-, hydrochloride (1:1)HCID 145852434-(Piperazin-1-yl)-2,6-di(pyrrolidin-1-yl)pyrimidine

Product 1

HCID 53833167HCID 53833167, compound

Reagents, catalysts & solvents 3

HCID 6342
Acetonitrile
Solvent
HCID 6344DichloromethaneSolvent3×
HCID 8471TriethylamineSolvent

Procedure

To 2,6-dimethyl-4-aminophenol hydrogen chloride (5.0 g) in methylene chloride (20 ml) is added triethylamine (6.5 g) in methylene chloride (20 ml) dropwise at 0°. To the cold solution is added chloroacetylchloride (3.6 g) in methylene chloride (20 ml) dropwise over 5-10 m. The mixture is stirred at 0° for 30 min and then at 20°-25° for 1 hr. The mixture is washed with water (60 ml), dried over sodium sulfate and the solvent removed at reduced pressure to give a solid. MS (EI, m/e)=213, 215 (M+). Acetonitrile (40 ml), 2,6-bis(1-pyrrolidinyl)-4-(1-piperazinyl)pyrimidine (PREPARATION A-22, 1.42 g), potassium carbonate (0.65 g) are added to the solid and the mixture is heated at reflux for 10 hr. The solvent is removed at reduced pressure and residue is distributed between chloroform (100 ml) and water (100 ml). The phases are separated and the organic phase is dried over sodium sulfate and the solvent is removed at reduced pressure to give an oil. The oil is flash chromatographed on silica gel (175 g) eluting with ethyl acetate/hexane (2/1). The appropriate fractions were pooled and concentrated to give the title compound.

Workup

  1. waitat 20°-25° for 1 hr
  2. washThe mixture is washed with water (60 ml)
  3. dry with materialdried over sodium sulfate
  4. customthe solvent removed at reduced pressure
  5. customto give a solid
  6. temperaturethe mixture is heated
  7. temperatureat reflux for 10 hr
  8. customThe solvent is removed at reduced pressure and residue
  9. customThe phases are separated
  10. dry with materialthe organic phase is dried over sodium sulfate
  11. customthe solvent is removed at reduced pressure
  12. customto give an oil
  13. customchromatographed on silica gel (175 g)
  14. washeluting with ethyl acetate/hexane (2/1)
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-a2e680aa9e224f61a1e095384845d71f
Source dataset
uspto-grants-1992_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05120843

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes