Formaldehyde → 4,4-Diaminodiphenylmethane

HRID 1071898Notes

Reaction equation

HRID 1071898 reaction equation
[NH2:1][C:2]1[C:3](S(O)(=O)=O)=[CH:4][CH:5]=[CH:6][CH:7]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15](S(O)(=O)=O)[CH:14]=1.N[C:24]1C=CC=CC=1.C=O>>[CH:15]1[C:16]([CH2:24][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)=[CH:17][CH:18]=[C:13]([NH2:12])[CH:14]=1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 6115AnilineHCID 69262-Aminobenzenesulfonic acidHCID 84743-Aminobenzenesulfonic acid

Product 1

HCID 75774,4-Diaminodiphenylmethane

Procedure

An 2-anilinesulfonic acid derivative (e.g. sodium 2-anilinesulfonate) or an 3-anilinesulfonic acid derivative (e.g. sodium 3-anilinesulfonate) and aniline are treated with formalin under acidic conditions, to give the corresponding 4,4′-diaminodiphenylmethane derivative. This is diazotized using sodium nitrite under acidic conditions in the presence of hydrochloric acid, followed by reaction with sodium azide, to give the desired product.

Sources & evidence

ORD record
ord-3b7b4bce60214d3b840310dd43bc7824
Source dataset
uspto-grants-2005_06
Patent number
US06908719B1

Reaction notes

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