5-(1,3-Dioxolan-2-yl)-4-methylthiophene-2-carbaldehyde → N-(4-{2-[5-(1,3-dioxolan-2-yl)-4-methylthiophen-2-yl]vinyl}-1,3-thiazol-2-yl)acetamide

HRID 1892515Notes

Reaction equation

HRID 1892515 reaction equation
[Cl-].[C:2]([NH:5][C:6]1[S:7][CH:8]=[C:9]([CH2:11][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:10]=1)(=[O:4])[CH3:3].[O:31]1[CH2:35][CH2:34][O:33][CH:32]1[C:36]1[S:40][C:39]([CH:41]=O)=[CH:38][C:37]=1[CH3:43]>>[O:31]1[CH2:35][CH2:34][O:33][CH:32]1[C:36]1[S:40][C:39]([CH:41]=[CH:11][C:9]2[N:10]=[C:6]([NH:5][C:2](=[O:4])[CH3:3])[S:7][CH:8]=2)=[CH:38][C:37]=1[CH3:43]

Participants

3

Reactant 2

HCID 581120655-(1,3-Dioxolan-2-yl)-4-methylthiophene-2-carbaldehydeHCID 86092822[(2-Acetylaminothiazol-4-yl)methyl](triphenyl)phosphonium chloride

Product 1

HCID 86650016N-(4-{2-[5-(1,3-dioxolan-2-yl)-4-methylthiophen-2-yl]vinyl}-1,3-thiazol-2-yl)acetamideYield 74.7%

Procedure

In a similar manner as in Production Example 16, step 1, {[2-(acetylamino)-1,3-thiazol-4-yl]methyl}(triphenyl)phosphonium chloride (12.03 g, 26.56 mmol) and 5-(1,3-dioxolan-2-yl)-4-methylthiophene-2-carbaldehyde (3.51 g, 17.7 mmol) were condensed to give N-(4-{2-[5-(1,3-dioxolan-2-yl)-4-methylthiophen-2-yl]vinyl}-1,3-thiazol-2-yl)acetamide (4.450 g, 13.23 mmol, yield 74.7%) as a yellow solid.

Workup

  1. customcondensed

Sources & evidence

ORD record
ord-13161fecb2314148b131987ac0273b2a
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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