Ethanol → Imidazo(2,1-b)(1,3)thiazol-3-ylmethanol

HRID 635870Notes

Reaction equation

HRID 635870 reaction equation
FC1C=C(C=CC([C:12]2[N:19]3[C:15]([S:16][C:17]4CCCC[CH2:20][C:18]=43)=[N:14][CH:13]=2)=O)C=CC=1.[BH4-].[Na+].C([OH:29])C>>[S:16]1[CH:17]=[C:18]([CH2:20][OH:29])[N:19]2[CH:12]=[CH:13][N:14]=[C:15]12

Participants

4

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 700570593-(3-Fluorophenyl)-1-(6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-yl)-2-propene-1-one

Product 1

HCID 14801956Imidazo(2,1-b)(1,3)thiazol-3-ylmethanol

Procedure

3-(3-Fluorophenyl)-1-(6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-yl)-2-propene-1-one (Formula N-5, X=3-fluoro), 0.34 g, in ethanol (35 mL) was treated with NaBH4 (0.11 g), reacted for 3 hours, and solvent removed in vacuo. The residue was suspended in water, filtered and the filter cake was crystallized from acetonitrile to provide pure α-[2-(3-fluorophenyl) ethenyl]-6,7,8,9-tetrahydro-5H, imidazo[2,1-b]thiazole-3-methanol, 0.30 g, m.p. 175-176° (Formula N-8, X=3-fluoro).

Workup

  1. customreacted for 3 hours
  2. customsolvent removed in vacuo
  3. filtrationfiltered
  4. customthe filter cake was crystallized from acetonitrile

Sources & evidence

ORD record
ord-311bca339231446db1c622673b29056a
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

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