Water → 1-[5-(3-Amino-5-chlorophenyl)-1,3-thiazol-2-yl]cyclobutanol

HRID 1039994Notes

Reaction equation

HRID 1039994 reaction equation
O.[Cl:2][C:3]1[CH:4]=[C:5]([C:12]2[S:16][C:15]([C:17]3([OH:21])[CH2:20][CH2:19][CH2:18]3)=[N:14][CH:13]=2)[CH:6]=[C:7]([N+:9]([O-])=O)[CH:8]=1.[Cl-].[NH4+]>[Fe].C(O)C>[NH2:9][C:7]1[CH:6]=[C:5]([C:12]2[S:16][C:15]([C:17]3([OH:21])[CH2:20][CH2:19][CH2:18]3)=[N:14][CH:13]=2)[CH:4]=[C:3]([Cl:2])[CH:8]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 674321141-[5-(3-Chloro-5-nitrophenyl)-1,3-thiazol-2-yl]cyclobutanol

Product 1

HCID 674320031-[5-(3-Amino-5-chlorophenyl)-1,3-thiazol-2-yl]cyclobutanolYield 83.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Water (2.617 mL) and ethanol (5.235 mL) were added to the product of Step 2 (610 mg, 49.3%), followed by ammonium chloride (52.5 mg, 0.981 mmol) and then iron (548 mg, 9.81 mmol) and the reaction was heated to 80° C. for 1 hour. The reaction mixture was filtered and diluted with ethyl acetate before washing with water, filtering off solids and drying over Na2SO4. Filtration and solvent evaporation gave a residue which was further purified by column chromatography on silica gel, eluting with ethyl acetate/hexane with a gradient 40-50% to afford 1-[5-(3-amino-5-chlorophenyl)-1,3-thiazol-2-yl]cyclobutanol (460 mg, 83%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. additiondiluted with ethyl acetate
  3. washbefore washing with water
  4. filtrationfiltering off solids
  5. dry with materialdrying over Na2SO4
  6. filtrationFiltration and solvent evaporation
  7. customgave a residue which
  8. customwas further purified by column chromatography on silica gel
  9. washeluting with ethyl acetate/hexane with a gradient 40-50%

Sources & evidence

ORD record
ord-6cbb3728f8f546da9faf37c59f919cf4
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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