1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-(Azidomethyl)-4-methylthiazole

HRID 2070921Notes

Reaction equation

HRID 2070921 reaction equation
C1(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2.[CH3:29][C:30]1[N:31]=[C:32]([CH2:35]O)[S:33][CH:34]=1>C1(C)C=CC=CC=1>[N:15]([CH2:35][C:32]1[S:33][CH:34]=[C:30]([CH3:29])[N:31]=1)=[N+:16]=[N-:17]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 17750909(4-Methyl-1,3-thiazol-2-yl)methanol

Product 1

HCID 574866712-(Azidomethyl)-4-methylthiazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Diphenylphosphoryl azide (DPPA) (1.2 eq) and 1,8-Diazabicyclo(5.4.0)undec-7-ene (DBU) (1.2 eq) were added to a stirred solution of (4-methylthiazol-2-yl)methanol (1 eq) in 7 ml anh. toluene under Ar. After stirring overnight, the solvent was removed in vacuo. Purification via flash chromatography yielded 2-(azidomethyl)-4-methylthiazole.

Workup

  1. customthe solvent was removed in vacuo
  2. customPurification via flash chromatography

Sources & evidence

ORD record
ord-4642ff2254764fa3b2e2ad8466bf9080
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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