Triethylamine → HCID 59646786, compound

HRID 1365747Notes

Reaction equation

HRID 1365747 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH2:7]O)=[CH:5][N:6]=1.CS(Cl)(=O)=O.C(N(CC)CC)C.[N-:21]=[N+:22]=[N-:23].[Na+]>O1CCCC1.CN(C)C=O.C(OCC)(=O)C>[N:21]([CH2:7][C:4]1[S:3][C:2]([CH3:1])=[N:6][CH:5]=1)=[N+:22]=[N-:23]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 12808792(2-Methyl-1,3-thiazol-5-yl)methanol

Product 1

HCID 59646786HCID 59646786, compoundYield 92.8%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (2-methylthiazol-5-yl)methanol (3.99 g, 30.9 mmol) in tetrahydrofuran (100 ml) was cooled to 0° C. and treated with methanesulfonyl chloride (2.40 ml, 30.9 mmol) followed by triethylamine (4.3 ml, 30.9 mmol) added dropwise over 10 min. The resulting mixture was stirred for 20 min, diluted with N,N-dimethylformamide (50 ml) and then treated with sodium azide (3.20 g, 49.2 mmol). After 18 h at 22° C., the reaction mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate, brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent under reduced pressure followed by chromatography of the residue on silica gel (elution toluene-ethyl acetate 0-20%) gave 4.42 g (92% yield) of the title azide as a clear oil. 1HNMR 400 MHz (CDCl3) δ (ppm): 2.74 (3H, s, CH3), 4.50 (2H, s, CH2), 7.56 (1H, s, CH). MS (ESI+) m/e 155 [M+H+].

Workup

  1. additionadded dropwise over 10 min
  2. waitAfter 18 h at 22° C.
  3. washwashed with saturated sodium bicarbonate, brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-2aba0b3f78734af0b781f6205b338917
Source dataset
uspto-grants-2011_02
Patent number
US07893055B2

Reaction notes

Loading…