Water → HCID 11486936, compound

HRID 1392595Notes

Reaction equation

HRID 1392595 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([I:9])[CH:3]=1.[CH:10](O)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>C(#N)C.C1(S(O)(=O)=O)C=CC=CC=1>[CH:10]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[I:9])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 962WaterHCID 7037BenzhydrolHCID 27576154-Chloro-2-iodoaniline

Product 1

HCID 11486936HCID 11486936, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 7371Benzenesulfonic AcidCatalystHCID 6342AcetonitrileSolvent

Procedure

To a nitrogen purged 2 L three necked flask equipped with addition funnel, overhead stirrer and reflux condenser was charged 150 g(0.591 mol) 4-Chloro-2-iodo-phenylamine, 3 g(0.018 mol, 0.03 eq) benzenesulfonic acid and 500 mL acetontrile. The mixture was warmed to 70 C and 120 g (0.652 mol, 1.1 eq) benzhydrol dissolved in 500 mL acetonitrile was added to the stirred warm solution over a period of 7.5 h. After another 4 h, LC analysis showed 95% product and 5% starting material remaining. The mixture was cooled to 25 C and 290 mL water was added dropwise over a period of 30-40 min. Stirring was continued over night at 23 C. The dark purple solid was collected by filtration, washed with 2× withMeCN/water 1/1 dried at 50 C in vacuo for 15 h to give 218.5 g (88%) product.

Workup

  1. customTo a nitrogen purged 2 L three necked flask
  2. customequipped with addition funnel, overhead stirrer
  3. temperaturereflux condenser
  4. additionwas added to the stirred
  5. temperaturewarm solution over a period of 7.5 h
  6. additionwas added dropwise over a period of 30-40 min
  7. waitwas continued over night at 23 C
  8. filtrationThe dark purple solid was collected by filtration
  9. washwashed with 2× withMeCN/water 1/1
  10. customdried at 50 C in vacuo for 15 h

Sources & evidence

ORD record
ord-585870b95feb4210a14c0fa3bfff8525
Source dataset
uspto-grants-2008_03
Patent number
US07342119B2

Reaction notes

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