Water → HCID 22768144, compound

HRID 1763203Notes

Reaction equation

HRID 1763203 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11](=[O:14])[O:12][CH3:13])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[Na+].[Br:20]Br.O>C(O)(=O)C.C(O)=O.C(Cl)Cl>[Br:20][C:6]1[C:7]([NH:10][C:11](=[O:14])[O:12][CH3:13])=[N:8][O:9][C:5]=1[C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 962WaterHCID 24408Bromine2×HCID 517045Sodium Acetate2×HCID 13309592Methyl 5-tert-butyl-1,2-oxazol-3-ylcarbamate

Product 1

HCID 22768144HCID 22768144, compoundYield 99.1%

Reagents, catalysts & solvents 3

HCID 284Formic AcidCatalystHCID 176Acetic AcidSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 5-t-butyl-3-isoxazolyl-carbamate (2.00 g) and anhydrous sodium acetate (1.1 mol equivalent) in glacial acetic acid (5 ml), bromine (1.0 mol equivalent) is added. The resultant mixture is heated at 50° C. for 53 hours and mixed with glacial acetic acid (5 ml), anhydrous sodium acetate (0.91 g) and bromine (0.81 g). The mixture is heated at 70° C. for 31 hours, mixed with several drops of formic acid, poured onto icy water (50 ml) and shaken with methylene chloride. The organic layer is washed with a saturated aqueous solution of sodium bicarbonate and water in order and evaporated under reduced pressure to remove the solvent, whereby methyl 4-bromo-5-t-butyl-3-isoxazolyl-carbamate (2.77 g) is obtained as an oil. I.R.: 1774, 1203 cm-1 (CCl4).

Workup

  1. washThe organic layer is washed with a saturated aqueous solution of sodium bicarbonate and water in order
  2. customevaporated under reduced pressure
  3. customto remove the solvent

Sources & evidence

ORD record
ord-a095ff42e78b458aaef4d7929b1b7622
Source dataset
uspto-grants-1978_09
Patent number
US04111680

Reaction notes

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