2-Iodoaniline → 1-Iodo-2-isocyanatobenzene

HRID 1623480Notes

Reaction equation

HRID 1623480 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:8].Cl[C:10](Cl)([O:12]C(=O)OC(Cl)(Cl)Cl)Cl.C(=O)(O)[O-].[Na+]>ClCCl>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]=[C:10]=[O:12]

Participants

5

Reactant 3

HCID 119952-IodoanilineHCID 94429TriphosgeneHCID 516892Sodium Bicarbonate

Product 1

HCID 27333851-Iodo-2-isocyanatobenzeneYield 267.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-iodo-phenylamine (30 g, 0.14 mol) in dichloromethane (800 ml) was added triphosgene (14.6 g, 49.3 mmol) and saturated sodium bicarbonate (544 ml) at 0° C. The resulted mixture was stirred for 4 hours. The organic layer was washed with brine (200 ml) and dried over sodium sulfate. After removal of solvent, the crude product 1-iodo-2-isocyanato-benzene (32.3 g, 96%) was obtained as a yellow oil which was used in next step without purification.

Workup

  1. washThe organic layer was washed with brine (200 ml)
  2. dry with materialdried over sodium sulfate
  3. customAfter removal of solvent

Sources & evidence

ORD record
ord-cf8b5740a901430c8f02c32ac7d387a8
Source dataset
uspto-grants-2014_07
Patent number
US08778973B2

Reaction notes

Loading…