Benzhydrylamine → HCID 178522803, compound

HRID 864675Notes

Reaction equation

HRID 864675 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[N:3]=[CH:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.C(N(C(C)C)CC)(C)C.[NH2:30][CH:31]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C=O)C>[C:38]1([CH:31]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[NH:30][C:6]([C:4]2[N:3]=[CH:2][NH:1][CH:5]=2)=[O:8])[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

6

Reactant 4

HCID 7036BenzhydrylamineHCID 682631,1'-CarbonyldiimidazoleHCID 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'-carbonyldiimidazole, 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 n vacuo. Two crystallizations from hot ethyl acetate/hexane provided 11 grams of the desired titled intermediate, m.p. 201°-202° C.

Workup

  1. concentrationwas 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 n vacuo
  7. customTwo crystallizations from hot ethyl acetate/hexane

Sources & evidence

ORD record
ord-6431a5f0d7b540a2bd2111642704e227
Source dataset
uspto-grants-1996_10
Patent number
US05563278

Reaction notes

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