Ethyl isocyanoacetate → HCID 19768806, compound

HRID 1590881Notes

Reaction equation

HRID 1590881 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10](OC)=[S:11].[N+:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])#[C-:21]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][O:6][C:7]1[CH:8]=[C:9]([C:10]2[S:11][CH:21]=[N:20][C:22]=2[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:14]=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 533707Ethyl isocyanoacetateHCID 19768753HCID 19768753, compound

Product 1

HCID 19768806HCID 19768806, compoundYield 77.8%

Procedure

In an analogous manner to that described in Example 1(C), 28.2 g (96.3 mmol) of O-methyl 3-[(3-chlorobenzyl)-oxy]thiobenzoate were reacted with ethyl isocyanoacetate and subsequently chromatographed on silica gel. Elution with 9:1, 8:2 and 1:1 mixtures of methylene chloride and ethyl acetate as well as ethyl acetate along yielded 28 g (77.8%) of ethyl 5-[3-[(3-chlorobenzyl)oxy]phenyl]-4-thiazolecarboxylate as an orange oil.

Workup

  1. customsubsequently chromatographed on silica gel
  2. washElution with 9:1, 8:2 and 1:1 mixtures of methylene chloride and ethyl acetate as well as ethyl acetate

Sources & evidence

ORD record
ord-dfcc532e14f644d78889bf3efcb63935
Source dataset
uspto-grants-1993_04
Patent number
US05204482

Reaction notes

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