Triacetoxyperiodinane → 1-(3-Fluorobenzyl)-3-(4-formylthiazol-2-yl)urea

HRID 1685054Notes

Reaction equation

HRID 1685054 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][NH:6][C:7]([NH:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][OH:16])[N:14]=1)=[O:8].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][NH:6][C:7]([NH:9][C:10]1[S:11][CH:12]=[C:13]([CH:15]=[O:16])[N:14]=1)=[O:8]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86661282(3-Fluoro-benzyl)-3-(4-hydroxymethyl-thiazol-2-yl)-urea

Product 1

HCID 580550461-(3-Fluorobenzyl)-3-(4-formylthiazol-2-yl)ureaYield 64.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3-Fluoro-benzyl)-3-(4-hydroxymethyl-thiazol-2-yl)-urea (909.52 mg) was added in a solution of Dess-Martin periodinane (0.3 M, 10.8 mL) in DCM (100 mL) at 0° C. The reaction mixture was stirred at room temperature over a couple of hours until all starting materials were consumed. After concentration, the residue was recrystallized from DCM/Hexane to afford the desired product (580 mg).

Workup

  1. customwere consumed
  2. concentrationAfter concentration
  3. customthe residue was recrystallized from DCM/Hexane

Sources & evidence

ORD record
ord-eac16c20c59445d3a41f426947f8bb57
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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