Cyclooctyl isocyanate → 4-bromo-N-(2,2,2-trichloro-1-(cyclooctylamino)ethyl)furan-2-carboxamide

HRID 1920093Notes

Reaction equation

HRID 1920093 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.[N:16]([CH:19]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=C=O>C1C=CC=CC=1.C(N(CC)CC)C>[Br:1][C:2]1[CH:3]=[C:4]([C:7]([NH:9][CH:10]([NH:16][CH:19]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:11]([Cl:14])([Cl:13])[Cl:12])=[O:8])[O:5][CH:6]=1

Participants

5

Reactant 2

HCID 12393370Cyclooctyl isocyanateHCID 581495354-bromo-N-(2,2,2-trichloro-1-hydroxyethyl)furan-2-carboxamide

Product 1

HCID 581495294-bromo-N-(2,2,2-trichloro-1-(cyclooctylamino)ethyl)furan-2-carboxamideYield 67.7%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 241BenzeneSolvent

Procedure

4-Bromo-N-(2,2,2-trichloro-1-hydroxyethyl)furan-2-carboxamide 125 (0.16 g, 0.47 mmol) and isocyanatocyclooctane (0.08 mL, 0.51 mmol) in benzene (2 mL) with triethyl amine (2 drops) was heated to 95° C. for 1.5 hours. The mixture was concentrated onto silica gel and purified by chromatography (7:3 to 6:4 hexane:CH2Cl2) to give 4-bromo-N-(2,2,2-trichloro-1-(cyclooctylamino)ethyl)furan-2-carboxamide (Compound-51) (142 mg, 67%). 1H NMR (300 MHz, CDCl3): δ=7.50 (d, J=0.9 Hz, 1H), 7.21 (d, J=0.9 Hz, 1H), 6.59 (d, J=9.6 Hz, 1H), 5.55 (t, J=9.3 Hz, 1H), 2.96-2.85 (m, 1H), 1.79-1.42 (m, 15H).

Workup

  1. concentrationThe mixture was concentrated onto silica gel
  2. custompurified by chromatography (7:3 to 6:4 hexane:CH2Cl2)

Sources & evidence

ORD record
ord-eb4da2a0233d4ec2965e20699af118d8
Source dataset
uspto-grants-2012_05
Patent number
US08168795B2

Reaction notes

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