4,4-Diaminodiphenylmethane → HCID 14806250, compound

HRID 1493461Notes

Reaction equation

HRID 1493461 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.[CH3:16][C:17]([O:20][C:21](ON=C(C1C=CC=CC=1)C#N)=[O:22])([CH3:19])[CH3:18]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[O:20]([C:21]([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)=[O:22])[C:17]([CH3:19])([CH3:18])[CH3:16]

Participants

5

Reactant 2

HCID 75774,4-DiaminodiphenylmethaneHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

Product 1

HCID 14806250HCID 14806250, compoundYield 553%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

This synthesis again starts with a monoprotected diamine. To a solution consisting of 8.0 g (40 mmol) 4,4'-methylenedianiline in 60 ml dry chloroform and 0.85 ml triethylamine is added dropwise a solution of 1 g BOC-ON dissolved in 20 ml chloroform. This reaction is allowed to stir at room temperature for 6 days. The reaction mixture is then filtered and the filtrate evaporated to a solid. This solid is then purified by silica gel column chromatography (70% petroleum ether/30% ethyl acetate as eluant) to give 6.7 g (55%) of N-(t-butoxylcarbonyl)-4,4'methylenedianiline.

Workup

  1. customThis synthesis
  2. filtrationThe reaction mixture is then filtered
  3. customthe filtrate evaporated to a solid
  4. customThis solid is then purified by silica gel column chromatography (70% petroleum ether/30% ethyl acetate as eluant)

Sources & evidence

ORD record
ord-3c0f1255821847159864e281a626218f
Source dataset
uspto-grants-1991_06
Patent number
US05021571

Reaction notes

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