Benzhydrylamine → HCID 178522803, compound

HRID 1461095Notes

Reaction equation

HRID 1461095 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[N:3]=[CH:2]1.C(N(C(C)C)CC)(C)C.[NH2:18][CH:19]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[C:26]1([CH:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:18][C:6]([C:4]2[N:3]=[CH:2][NH:1][CH:5]=2)=[O:8])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 7036BenzhydrylamineHCID 81531DiisopropylethylamineHCID 178524800HCID 178524800, compound

Product 1

HCID 178522803HCID 178522803, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 11.7 g of 4-imidazolecarboxylic acid, 18.7 g of 1,1'-carbonyldiidmidazole, 20 ml of diisopropylethylamine and 600 ml of DMF was heated at 35° C. for approximately 18 hours. Twenty milliters of aminodiphenylmethane were added and the solution stirred at 35° C. for approximately 21/2 days. The mixture was concentrated in vacuo and the residue added to 400 ml of water. The mixture was extracted with ethyl acetate and the organic layer was washed with a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. Two crystallizations from hot ethyl acetate/hexane provided 11 grams of the desired titled intermediate, m.p. 201°-202° C.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue added to 400 ml of water
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with a saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customTwo crystallizations from hot ethyl acetate/hexane

Sources & evidence

ORD record
ord-ceb4ef36184e4f318931e0ee893d5c5b
Source dataset
uspto-grants-1991_12
Patent number
US05073566

Reaction notes

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