N-BOC-ethylenediamine → t-Butyl [2-(2-chloro-5-phenyl-4-thiazolecarboxamido)ethyl]carbamate

HRID 1590885Notes

Reaction equation

HRID 1590885 reaction equation
[Cl:1][C:2]1[S:3][C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:5]([C:7]([O:9]C)=O)[N:6]=1.[NH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24]>>[Cl:1][C:2]1[S:3][C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:5]([C:7]([NH:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:9])[N:6]=1

Participants

3

Reactant 2

HCID 187201N-BOC-ethylenediamineHCID 12821997Methyl 2-chloro-5-phenyl-4-thiazolecarboxylate2×

Product 1

HCID 54568294t-Butyl [2-(2-chloro-5-phenyl-4-thiazolecarboxamido)ethyl]carbamateYield 27.5%

Procedure

5.4 g (21.3 mmol) of methyl 2-chloro-5-phenyl-4-thiazolecarboxylate and 3.6 g (22.3 mmol) of t-butyl (2-aminoethyl)carbamate were stirred under reduced pressure for 22 hours at a bath temperature of 110°, whereby the methanol formed was distilled off continuously. The reaction mixture was cooled, dissolved in methylene chloride and chromatographed on 150 g of silica gel with methylene chloride and a 4:1 mixture of methylene chloride and ethyl acetate as the eluting agent. The fractions which were pure according to the thin-layer chromatogram were combined and evaporated. Crystallization of the residue from ethyl acetate/hexane yields 1.83 g (27.5%) of t-butyl [2-(2-chloro-5-phenyl-4-thiazolecarboxamido)ethyl]carbamate as white crystals, melting point 114°-116°.

Workup

  1. customformed
  2. distillationwas distilled off continuously
  3. temperatureThe reaction mixture was cooled
  4. dissolutiondissolved in methylene chloride
  5. customchromatographed on 150 g of silica gel with methylene chloride
  6. additiona 4:1 mixture of methylene chloride and ethyl acetate as the eluting agent
  7. customevaporated
  8. customCrystallization of the residue from ethyl acetate/hexane

Sources & evidence

ORD record
ord-52774703c790460794ca29833be50edb
Source dataset
uspto-grants-1993_04
Patent number
US05204482

Reaction notes

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