3-Iodoaniline → HCID 21867065, compound

HRID 857101Notes

Reaction equation

HRID 857101 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Cl[CH2:10][CH2:11][N:12]=[C:13]=[O:14]>C(Cl)Cl.C(N(C(C)C)CC)(C)C.CCOC(C)=O>[I:1][C:2]1[CH:3]=[C:4]([N:5]2[CH2:10][CH2:11][NH:12][C:13]2=[O:14])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 122713-IodoanilineHCID 160352-Chloroethyl isocyanate

Product 1

HCID 21867065HCID 21867065, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 3-iodoaniline (1 g) in CH2Cl2 (5 ml) and diisopropylethylamine (2 ml) was treated with 2-chloroethylisocyanate (0.4 ml) and the mixture was stirred at 20° C. for 3 d. The mixture was diluted with EtOAc and washed with 2M HCl, dried and evaporated to dryness. The residue was dissolved in DMF (5 ml), treated with sodium hydride (60% oil dispersion, 182 mg), and the mixture was stirred for 20 h under nitrogen. The mixture was diluted with EtOAc, washed with 2M HCl, brine, dried and evaporated to dryness. The residue was crystallised from hot EtOAc/MeOH. Trituration in Et2O of the residue obtained by evaporation of the mother liquor gave the title compound (240 mg). LCMS RT=3.03 min.

Workup

  1. washwashed with 2M HCl
  2. customdried
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in DMF (5 ml)
  5. additiontreated with sodium hydride (60% oil dispersion, 182 mg)
  6. stirringthe mixture was stirred for 20 h under nitrogen
  7. additionThe mixture was diluted with EtOAc
  8. washwashed with 2M HCl, brine
  9. customdried
  10. customevaporated to dryness
  11. customThe residue was crystallised from hot EtOAc/MeOH
  12. customTrituration in Et2O of the residue obtained by evaporation of the mother liquor

Sources & evidence

ORD record
ord-2ee22d3901084519a5b16804129b6d3d
Source dataset
uspto-grants-2006_12
Patent number
US07144908B2

Reaction notes

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