Acetic Acid → 4-Ethyl-5-iodo-thiazol-2-ylamine

HRID 1009038Notes

Reaction equation

HRID 1009038 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]([NH2:8])[S:6][CH:7]=1)[CH3:2].C(O)(=O)C.[I:13]Cl>C(Cl)Cl>[CH2:1]([C:3]1[N:4]=[C:5]([NH2:8])[S:6][C:7]=1[I:13])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24640Iodine chlorideHCID 123782054-Ethyl-1,3-thiazol-2-amine

Product 1

HCID 866309544-Ethyl-5-iodo-thiazol-2-ylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Ethyl-thiazol-2-ylamine (0.960 g, 7.49 mmol) was dissolved in 17 mL of CH2Cl2 and 3.5 mL of acetic acid and treated at 0° C. with iodine monochloride (7.86 mL of 1M in CH2Cl2, 1.05 eq.) and kept at this temperature for 1 h. Pouring onto crashed ice/Na2CO3, twofold extraction with ethyl acetate, washing with water and brine, drying over sodium sulfate, and evaporation to dryness afforded 1.67 g of the title compound as almost black viscous oil, sufficiently pure to be used for the next step.

Workup

  1. additionPouring
  2. extractionice/Na2CO3, twofold extraction with ethyl acetate
  3. washwashing with water and brine
  4. dry with materialdrying over sodium sulfate, and evaporation to dryness

Sources & evidence

ORD record
ord-f031df9c99f847b1ab07e953b1a0a23c
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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