4,4-Diaminodiphenylmethane → HCID 53937821, compound

HRID 723562Notes

Reaction equation

HRID 723562 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-6015afcf710f4e8eab87d7020a8eb009
Source dataset
uspto-grants-2006_11
Patent number
US07141584B2

Reaction notes

Loading…