Dichloromethane → HCID 19768809, compound

HRID 1085848Notes

Reaction equation

HRID 1085848 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([C:8]2[S:12][CH:11]=[N:10][C:9]=2[C:13]([NH:15][CH2:16][CH2:17][NH:18]C(=O)OC(C)(C)C)=[O:14])[CH:5]=[CH:6][CH:7]=1.FC(F)(F)C(O)=O.C(Cl)[Cl:34]>>[ClH:34].[NH2:18][CH2:17][CH2:16][NH:15][C:13]([C:9]1[N:10]=[CH:11][S:12][C:8]=1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([I:1])[CH:3]=1)=[O:14]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 54091391HCID 54091391, compound

Product 1

HCID 19768809HCID 19768809, compoundYield 88%

Procedure

6.3 g (13.3 mmol) of t-butyl [2-[5-(3-iodophenyl)-4-thiazolecarboxamido]ethyl]carbamate were dissolved in 70 ml of methylene chloride, treated with 5.1 ml of trifluoroacetic acid and stirred under reflux for 2 hours. Subsequently, the mixture was concentrated under reduced pressure. The residue was dissolved in 50 ml of methanol and treated with 5.2 ml of 2.7N ethanolic hydrochloric acid, whereby 4.8 g (88%) of N-(2-aminoethyl)-5-(3-iodophenyl)-4-thiazolecarboxamide hydrochloride were obtained as white crystals, melting point 272°-273°.

Workup

  1. temperatureunder reflux for 2 hours
  2. concentrationSubsequently, the mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 50 ml of methanol
  4. additiontreated with 5.2 ml of 2.7N ethanolic hydrochloric acid

Sources & evidence

ORD record
ord-cb0ae48d47a7468bafc4eec424c89855
Source dataset
uspto-grants-1991_04
Patent number
US05011849

Reaction notes

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