4-Chlorophenyl Isocyanate → 4-bromo-N-(2,2,2-trichloro-1-(4-chlorophenylamino)ethyl)furan-2-carboxamide

HRID 554714Notes

Reaction equation

HRID 554714 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:7]([NH:9][CH:10](O)[C:11]([Cl:14])([Cl:13])[Cl:12])=[O:8])[O:5][CH:6]=1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=C=O)=[CH:19][CH:18]=1>C(N(CC)CC)C.C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:7]([NH:9][CH:10]([NH:23][C:20]2[CH:21]=[CH:22][C:17]([Cl:16])=[CH:18][CH:19]=2)[C:11]([Cl:14])([Cl:13])[Cl:12])=[O:8])[O:5][CH:6]=1

Participants

5

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 581495354-bromo-N-(2,2,2-trichloro-1-hydroxyethyl)furan-2-carboxamide

Product 1

HCID 448146464-bromo-N-(2,2,2-trichloro-1-(4-chlorophenylamino)ethyl)furan-2-carboxamide

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 241BenzeneSolvent

Procedure

was prepared in accordance with reported methods: see Ulrich, H. et al J Org. Chem., 33, 1968, 2887. A solution of 4-bromo-N-(2,2,2-trichloro-1-hydroxyethyl)furan-2-carboxamide (preparation as for 6 above) (0.566 g, 1.67 mmol), 1-chloro-4-isocyanato-benzene (0.264 g, 1.68 mmol) and triethylamine (2 drops) in benzene (4 mL) was heated at 95° C. for 1.5 h. The mixture was evaporated under reduced pressure. The residue was solvated with chloroform and concentrated onto silica gel. Chromatographic purification on an auto-column with 30% dichloromethane in hexanes gave 4-bromo-N-(2,2,2-trichloro-1-(4-chlorophenylamino)ethyl)furan-2-carboxamide (Compound 33) as a white solid; 422 mg (57%).

Workup

  1. customwas prepared in accordance
  2. customThe mixture was evaporated under reduced pressure
  3. concentrationconcentrated onto silica gel
  4. customChromatographic purification on an auto-column with 30% dichloromethane in hexanes

Sources & evidence

ORD record
ord-400d02ae3a6c4241a05bea9857716e06
Source dataset
uspto-grants-2011_11
Patent number
US08049037B2

Reaction notes

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