Acetic Acid → 5-Iodo-4-phenyl-thiazol-2-ylamine

HRID 1009044Notes

Reaction equation

HRID 1009044 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([NH2:12])[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C.[I:17]Cl>C(Cl)Cl>[I:17][C:11]1[S:10][C:9]([NH2:12])=[N:8][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24640Iodine chlorideHCID 403022-Amino-4-phenylthiazole

Product 1

HCID 866309575-Iodo-4-phenyl-thiazol-2-ylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Phenyl-thiazol-2-ylamine (0.881 g, 5.00 mmol) was dissolved in 10 mL of CH2Cl2 and 2 mL of acetic acid and treated at 0° C. with iodine monochloride (5.25 mL of 1M in CH2Cl2, 1.05 eq.) and kept at this temperature for 0.5 h. Pouring onto crashed ice/Na2CO3, twofold extraction with ethyl acetate, washing with water and brine, drying over sodium sulfate, and evaporation to dryness produced 1.60 g of the title compound as dark brown gum, 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-4fa2a604077d41d38d9be64e2e349ae8
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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