3-Hydroxyphenacyl bromide → HCID 18537150, compound

HRID 2298639Notes

Reaction equation

HRID 2298639 reaction equation
[NH2:1][C:2](=[S:15])[C:3]1[CH:4]=[C:5]([C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])[S:6][C:7]=1[CH3:8].Br[CH2:17][C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=1)=O>>[OH:26][C:22]1[CH:21]=[C:20]([C:18]2[N:1]=[C:2]([C:3]3[CH:4]=[C:5]([C:9]([O:11][CH:12]([CH3:13])[CH3:14])=[O:10])[S:6][C:7]=3[CH3:8])[S:15][CH:17]=2)[CH:25]=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 69172063-Hydroxyphenacyl bromideHCID 18537366HCID 18537366, compound

Product 1

HCID 18537150HCID 18537150, compound

Procedure

A solution of 1.97 g (8.1 mmol) of isopropyl 4-(aminothioxomethyl)-5-methylthiophene-2-carboxylate was reacted with 1.74 g (8.1 mmol) of 3′-hydroxy-2-bromoacetophenone (Example 40, step (a)) were reacted in a manner similar to Example 8, step (a) to give, after column chromatography on silica gel eluting with hexane:ethyl acetate 7/3 (v:v), crystallization from acetonitrile, and recrystallization from hexanes, isopropyl 4-[4-(3-hydroxyphenyl)(1,3-thiazol-2-yl)]-5-methylthiophene-2-carboxylate (1.4 g, 48%) as brown solid. 1H-NMR (DMSO-d6; 300 MHz) δ9.57 (br s, 1H), 8.14 (s, 1H), 8.08 (s, 1H), 7.46 (m, 2H), 7.26 (m, 1H), ), 6.78 (m, 1H), 5.12 (septet, 1H, J=6.2 Hz), 2.85 (s, 3H), 1.33 (d, 6H, J=6.2 Hz). Mass spectrum (ESI, m/z): Calcd. for C18H17NO3S2 360.1 (M+H), found 360.1.

Workup

  1. customwere reacted in a manner similar to Example 8, step (a)
  2. customto give
  3. customafter column chromatography on silica gel eluting with hexane:ethyl acetate 7/3 (v:v), crystallization
  4. customfrom acetonitrile, and recrystallization from hexanes, isopropyl 4-[4-(3-hydroxyphenyl)(1,3-thiazol-2-yl)]-5-methylthiophene-2-carboxylate (1.4 g, 48%) as brown solid

Sources & evidence

ORD record
ord-e0d3357d1d3345baa816552abe787214
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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