Bromoacetic Acid → HCID 22220859, compound

HRID 1836733Notes

Reaction equation

HRID 1836733 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]([OH:8])[CH3:7].[Br:9][CH2:10][C:11](O)=[O:12].C(#N)C>C(#N)C.CO>[Br-:9].[CH3:7][CH:6]1[C:2]2[S:1][CH:5]=[CH:4][N+:3]=2[CH2:10][C:11](=[O:12])[O:8]1

Participants

5

Reactant 3

HCID 6227Bromoacetic AcidHCID 6342AcetonitrileHCID 99892952-Thiazolemethanol, alpha-methyl- (7CI,9CI)

Product 1

HCID 22220859HCID 22220859, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 21959252Acetonitrile methanolSolvent

Procedure

1-(2-Thiazolyl)ethanol (0.5 g, 3.87 mmole), bromoacetic acid (0.537 g, 3.86 mmole), and acetonitrile (0.125 mL) were heated in an oil bath with stirring at 105 C. for 6 hr. The mixture was dissolved in 5 mL 4:1 acetonitrile/methanol and stored at 4 C. for 17 hr. The crystals which separated were filtered out and combined from two identical runs, and recrystalized from methanol/acetonitrile/ether to give a total of 0.32 g of the title compound, mp 214-215.5 C. Calcd for C7H8NO2SBr: C 33.5; H 3.20; N 5.59; found: C 33.62; H 3.16; N 5.61.

Workup

  1. waitfor 17 hr
  2. customThe crystals which separated
  3. filtrationwere filtered out
  4. customrecrystalized from methanol/acetonitrile/ether

Sources & evidence

ORD record
ord-876c05a7c0c04c07ab773ebccf6a47fe
Source dataset
uspto-grants-2004_08
Patent number
US06777557B2

Reaction notes

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