Ethyl chloroformate → HCID 18771867, compound

HRID 460208Notes

Reaction equation

HRID 460208 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([OH:9])=O)[N:6]=1.ClC(OCC)=O.[N-:16]=[N+:17]=[N-:18].[Na+]>C1COCC1.O>[Br:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([N:16]=[N+:17]=[N-:18])=[O:9])[N:6]=1

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 27632092-Bromo-1,3-thiazole-4-carboxylic acid

Product 1

HCID 18771867HCID 18771867, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-bromo-thiazole-4-carboxylic acid (5.33 g, 25.7 mmol) in anhydrous THF (40 mL) at 0° C., under N2, TEA (7.18 mL, 51.5 mmol) was added. After 30 min ethyl chloroformate (2.59 mL, 27.0 mmol) was added dropwise over 10 min. After 25 min a solution of NaN3 (1.76 g, 27.0 mmol) in H2O (12 mL) was added. The mixture was warmed to RT over 1 h then diluted with H2O (100 mL). The precipitate was filtered off and air dried to yield the title compound as a white amorphous solid. MS m/z: 233.2, 235.2 (M+H). Calc'd. for C4HBrN4OS-233.05.

Workup

  1. filtrationThe precipitate was filtered off
  2. customair dried

Sources & evidence

ORD record
ord-cf9dc9236b734fa09c0fcadd922ad53a
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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