Triethylamine → 2-Azidomethyl-4-bromo-thiazole

HRID 415010Notes

Reaction equation

HRID 415010 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH2:7]O)[S:5][CH:6]=1.FC(F)(F)S(Cl)(=O)=O.CCN(CC)CC.[N-:24]=[N+:25]=[N-:26].[Na+]>CN(C=O)C.O>[N:24]([CH2:7][C:4]1[S:5][CH:6]=[C:2]([Br:1])[N:3]=1)=[N+:25]=[N-:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 33557Sodium AzideHCID 79000Trifluoromethanesulfonyl chlorideHCID 11041630(4-Bromo-1,3-thiazol-2-yl)methanol

Product 1

HCID 579856112-Azidomethyl-4-bromo-thiazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(4-Bromo-thiazol-2-yl)-methanol (1.1 g, 5.7 mmol) in DMF (15 ml) is treated at room temperature under nitrogen atmosphere with trifluoromethanesulfonyl chloride (0.61 ml, 1 equivalent), and Et3N (0.8 ml, 1 equivalent). The reaction mixture is stirred for 3 hours at room temperature before the addition of sodium azide (1.11 g, 3 equivalents), followed by overnight stirring at the same temperature. The reaction mixture is diluted with water and extracted with DCM and diethyl ether. The combined organic extracts are dried (MgSO4) and concentrated under reduced pressure to afford the crude product, which is used without purification in the next step.

Workup

  1. extractionextracted with DCM and diethyl ether
  2. dry with materialThe combined organic extracts are dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8a323b20ed364551a6b9fa1a96b21976
Source dataset
uspto-grants-2012_01
Patent number
US08088766B2

Reaction notes

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