2-Aminothiophenol → Ethyl 2-(4-(benzo[d]thiazol-2-yl)-2-methoxyphenoxy)-2-methylpropanoate

HRID 338812Notes

Reaction equation

HRID 338812 reaction equation
[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]([CH3:15])([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([O:18][CH3:19])[CH:4]=1)=O.[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[SH:27]>CN(C=O)C>[S:27]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]=[C:1]1[C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]([CH3:15])([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([O:18][CH3:19])[CH:4]=1

Participants

4

Reactant 2

HCID 87132-AminothiophenolHCID 71497692Ethyl 2-(4-formyl-2-methoxyphenoxy)-2-methylpropanoate

Product 1

HCID 68279194Ethyl 2-(4-(benzo[d]thiazol-2-yl)-2-methoxyphenoxy)-2-methylpropanoateYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a DMF (3 mL) solvent in the presence of Na2S2O5 (136.1 mg, 0.71 mmol), a solution including Compound 122a (188.7 mg, 0.71 mmol) and 2-aminothiophenol (0.08 mL, 0.71 mmol) was stirred at room temperature for 2 days. After DMF was evaporated, the residual was distributed between ethyl acetate and water. An organic layer was dried, filtered, and evaporated. The residual was purified by silica gel column chromatography using hexane and ethyl acetate (EtOAc) (7:1) to obtain Compound 122b (244.8 mg, 93%).

Workup

  1. customAfter DMF was evaporated
  2. customAn organic layer was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residual was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f58376a8940e47ecac92d44e90b8da97
Source dataset
uspto-grants-2014_11
Patent number
US08889881B2

Reaction notes

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