4,4-Diaminodiphenylmethane → HCID 53937821, compound

HRID 2121032Notes

Reaction equation

HRID 2121032 reaction equation
[CH2:1]([C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>C(OCC)(=O)C.O>[CH2:26]([O:25][C:23](=[O:24])[NH:13][C:12]1[CH:14]=[CH:15][C:9]([CH2:1][C:2]2[CH:3]=[CH:4][C:5]([NH2:6])=[CH:7][CH:8]=2)=[CH:10][CH:11]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 75774,4-DiaminodiphenylmethaneHCID 10387Benzyl chloroformateHCID 11430Potassium Carbonate

Product 1

HCID 53937821HCID 53937821, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4,4′-methylenedianiline (19.8 g), potassium carbonate (20 g) in ethyl acetate (300 mL) and water (200 mL) was stirred in an ice bath. Benzyl chloroformate (15 mL) was slowly added to the mixture. The resulting mixture was stirred for 1 hour, then the organic layer was separated, and the aqueous layer extracted with additional ethyl acetate. The combined organic extracts were washed with water and brine, dried (Na2SO4), and the solvent removed in vacuo. The crude mixture was isolated by column chromatography on silica gel, eluting with 30% ethyl acetate/hexanes, to give 4-(4-aminobenzyl)phenyl-carbamic acid benzyl ester as solid.

Workup

  1. stirringThe resulting mixture was stirred for 1 hour
  2. customthe organic layer was separated
  3. extractionthe aqueous layer extracted with additional ethyl acetate
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. customthe solvent removed in vacuo
  7. customThe crude mixture was isolated by column chromatography on silica gel
  8. washeluting with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-283e847c0f4a40a9b5b5758c5a5dcc49
Source dataset
uspto-grants-2004_02
Patent number
US06693200B2

Reaction notes

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