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

HRID 1685017Notes

Reaction equation

HRID 1685017 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)urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The 1-(3-fluorobenzyl)-3-(4-(hydroxymethyl)thiazol-2-yl) urea is taken up in DCM and cooled to 0° C. and Dess-Martin oxidant (1.1 equiv) was added. Stirred at ambient temperature for 1 hour. Washed with dilute Na2SO3. Removed solvent in vacuo to give 1-(3-fluorobenzyl)-3-(4-formylthiazol-2-yl)urea (used directly in next step).

Workup

  1. washWashed with dilute Na2SO3

Sources & evidence

ORD record
ord-ab8c7923fc5d4b48b1dc6e7832c8f4e3
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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