Triethylamine → Methyl (1,3-benzothiazol-2-yl)acetate

HRID 2099012Notes

Reaction equation

HRID 2099012 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].C(N(CC)CC)C.[CH3:16][O:17][C:18](=[O:23])[CH2:19][C:20](Cl)=O>C(OCC)C>[CH3:16][O:17][C:18](=[O:23])[CH2:19][C:20]1[S:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 87132-AminothiophenolHCID 123460Methyl malonyl chloride

Product 1

HCID 358756Methyl (1,3-benzothiazol-2-yl)acetateYield 82%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

3.2 mL (30 mmol) 2-Amino-thiophenol are dissolved in 100 mL diethylether and treated with 4.17 mL (1 eq.) triethylamine to yield a suspension, to which 3.21 mL (1 eq.) chlorocarbonyl-acetic methyl ester in 10 mL diethylether is added dropwise within 20 min. The resulting suspension is stirred and additional 2 h at room temperature, and the precipitate removed by filtration. The filtrate is evaporated and column chromatographed (silica gel, ethyl acetate/petroleum ether 1:2) to yield the desired product as a yellowish liquid (5.1 g, 82%).

Workup

  1. customto yield a suspension
  2. customthe precipitate removed by filtration
  3. customThe filtrate is evaporated
  4. customcolumn chromatographed (silica gel, ethyl acetate/petroleum ether 1:2)

Sources & evidence

ORD record
ord-e40e81ac9324486888f458ba1be74e4a
Source dataset
uspto-grants-2009_08
Patent number
US07569337B2

Reaction notes

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