Triethylamine → 2-methoxymethylbenzothiazole-5-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide

HRID 50208Notes

Reaction equation

HRID 50208 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[S:5][C:6]2[CH:12]=[CH:11][C:10]([C:13]([OH:15])=O)=[CH:9][C:7]=2[N:8]=1.S(Cl)(Cl)=O.[CH2:20]([O:22][C:23]([CH2:25][CH2:26][NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:24])[CH3:21].C(N(CC)CC)C>ClCCl.O1CCCC1>[C:28]1([N:27]([CH2:26][CH2:25][C:23]([O:22][CH2:20][CH3:21])=[O:24])[C:13]([C:10]2[CH:11]=[CH:12][C:6]3[S:5][C:4]([CH2:3][O:2][CH3:1])=[N:8][C:7]=3[CH:9]=2)=[O:15])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 10910393beta-Alanine, N-phenyl-, ethyl esterHCID 184125372-(Methoxymethyl)-1,3-benzothiazole-5-carboxylic acid

Product 1

HCID 184125442-methoxymethylbenzothiazole-5-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 1.6 g (7.2 mmol) of 2-methoxymethylbenzothiazole-5-carboxylic acid in 60 mL dichloromethane was mixed with 1.6 mL (22 mmol) of thionyl chloride and refluxed for 1 hour. The solid dissolved after 20 minutes. After distillation of the liquid components, the crude product was taken up in dichloromethane twice more and each time the solvent was distilled off. The crude acid chloride thus obtained was taken up in 50 mL of tetrahydrofuran, added dropwise to a mixture of 1.4 g (7.2 mmol) of N-(2-ethoxycarbonylethyl)aniline and 3.0 mL (21 mmol) of triethylamine in 50 mL of tetrahydrofuran and stirred overnight at room temperature. Then the solvent was distilled off in vacuo, the residue was taken up in 30 mL of dichloromethane, this solution was washed with water, and dried with sodium sulfate. After distillation of the solvent and flash chromatography (silica gel; gradient: dichloromethane/ethanol 98.5:1.5 to 80:20), the desired compound was isolated as a brownish oil. Yield: 2.05 (72% of theory); Rf value: 0.40 (silica gel; ethyl acetate/petroleum ether=1:1).

Workup

  1. temperaturerefluxed for 1 hour
  2. dissolutionThe solid dissolved after 20 minutes
  3. distillationAfter distillation of the liquid components
  4. distillationeach time the solvent was distilled off
  5. customThe crude acid chloride thus obtained
  6. distillationThen the solvent was distilled off in vacuo
  7. washthis solution was washed with water
  8. dry with materialdried with sodium sulfate
  9. distillationAfter distillation of the solvent and flash chromatography (silica gel; gradient: dichloromethane/ethanol 98.5:1.5 to 80:20)

Sources & evidence

ORD record
ord-6441a5a8402140b29f988f2409c53ee4
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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