Acetonitrile → HCID 11486936, compound

HRID 1177663Notes

Reaction equation

HRID 1177663 reaction equation
[CH:1](O)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(#[N:17])C.[Cl:18][C:19]1[CH:25]=[C:24]([I:26])[CH:23]=[CH:22][C:20]=1N>C1(S(O)(=O)=O)C=CC=CC=1.O>[CH:1]([NH:17][C:23]1[CH:22]=[CH:20][C:19]([Cl:18])=[CH:25][C:24]=1[I:26])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6342Acetonitrile2×HCID 7037BenzhydrolHCID 2829302-Chloro-4-iodoaniline

Product 1

HCID 11486936HCID 11486936, compound

Reagents, catalysts & solvents 2

HCID 7371Benzenesulfonic AcidCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A solution of benzhydrol (13.5 g, 73.3 mmol) and acetonitrile (56 mL) was added over 1 h to a warm (80° C.), stirred solution of 2-chloro-4-iodoaniline (16 g, 63.1 mmol), benzenesulfonic acid (0.323 g, 2.0 mmol) and acetonitrile (53 mL). The solution was maintained at 80° C. for an additional 2.5 h. The mixture was allowed to cool to room temperature. Water (31 mL) was added over 1 h to the stirred mixture. The mixture was stirred for 2 h at room temperature. The solid product was collected by filtration. The solid product was combined with methanol (67 mL) and warmed to reflux for 30 m. The mixture was allowed to cool to room temperature. The purified product was collected by filtration, washed with methanol (2×10 mL) and vacuum dried to give 22.3 g of benzhydryl-(4-chloro-2-iodo-phenyl)-amine with 99% purity (as determined by HPLC). Mp 107-110.

Workup

  1. temperatureThe solution was maintained at 80° C. for an additional 2.5 h
  2. temperatureto cool to room temperature
  3. filtrationThe solid product was collected by filtration
  4. temperaturewarmed
  5. temperatureto reflux for 30 m
  6. temperatureto cool to room temperature
  7. filtrationThe purified product was collected by filtration
  8. washwashed with methanol (2×10 mL) and vacuum
  9. customdried

Sources & evidence

ORD record
ord-12bbe0c4638c4d259e2c368a9ad03d21
Source dataset
uspto-grants-2010_11
Patent number
US07842837B2

Reaction notes

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