Hydrochloric Acid → HCID 14726996, compound

HRID 329395Notes

Reaction equation

HRID 329395 reaction equation
Br.Cl[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([NH2:17])[S:14][C:15]=2[CH3:16])=[CH:7][CH:6]=1.[C:18]1([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].Cl>C(OCC)(=O)C.C(OCC)(=O)C.CO.CCOCC.C(O)C>[C:18]1([N:28]2[CH2:33][CH2:32][N:31]([CH2:3][CH2:4][C:5]3[CH:10]=[CH:9][C:8]([C:11]4[N:12]=[C:13]([NH2:17])[S:14][C:15]=4[CH3:16])=[CH:7][CH:6]=3)[CH2:30][CH2:29]2)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1

Participants

11

Reactant 6

HCID 313Hydrochloric AcidHCID 13421-(1-Naphthyl)piperazineHCID 5238Sodium IodideHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 14726985HCID 14726985, compound

Product 1

HCID 14726996HCID 14726996, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

To a 35 ml round-bottomed flask equipped with condenser and N2 inlet were added 0.81 g (2.80 mmol) of 4-(4-(2-chloroethyl)phenyl)-2-amino-5-methylthiazole hydrobromide, 0.59 g (2.80 mmol) of N-(1-naphthyl)piperazine, 0.78 ml (5.60 mmol) of triethylamine, 0.30 g (2.80 mmol) of sodium carbonate, 2 mg of sodium iodide, and 10 ml of ethanol. The reaction was heated at reflux for 5 days, cooled, and the reaction taken up in ethyl acetate, washed with water and brine, dried over sodium sulfate, and evaporated to an oil. The oil was chromatographed on silica gel using ethyl acetate/methylene chloride as eluent to give a white solid. The solid was taken up in ethyl acetate/methanol, ether saturated with HCl added, the precipitate filtered, washed with ether, and dried to give a white solid, 0.82 g (54%), m.p. 160°-165° C.

Workup

  1. customTo a 35 ml round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 5 days
  4. temperaturecooled
  5. washwashed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated to an oil
  8. customThe oil was chromatographed on silica gel
  9. customto give a white solid
  10. filtrationthe precipitate filtered
  11. washwashed with ether
  12. customdried
  13. customto give a white solid, 0.82 g (54%), m.p. 160°-165° C.

Sources & evidence

ORD record
ord-80c719e6475347e6837b77931b0dc6a5
Source dataset
uspto-grants-1990_01
Patent number
US04891375

Reaction notes

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