N,N-Dimethylaniline → Methane

HRID 2412823Notes

Reaction equation

HRID 2412823 reaction equation
[CH3:1][S:2]([OH:5])(=O)=[O:3].[CH3:6][N:7]([CH3:16])[C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1.[CH3:17][N:18]([CH3:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:26]1(C)[CH:31]=[CH:30][C:29](S([O-])=O)=[CH:28][CH:27]=1.[Na+]>C(O)C>[CH4:1].[CH3:6][N:7]([CH3:16])[C:8]1[CH:15]=[CH:14][C:11]([C:12]2[C:30]([C:22]3[CH:23]=[CH:24][C:19]([N:18]([CH3:25])[CH3:17])=[CH:20][CH:21]=3)=[C:31]([S:2]([CH3:1])(=[O:5])=[O:3])[CH:26]=[CH:27][C:28]=2[CH3:29])=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 949N,N-DimethylanilineHCID 6395Methanesulfonic AcidHCID 74794-(Dimethylamino)BenzaldehydeHCID 2723791Sodium p-toluenesulfinate

Product 2

HCID 297MethaneHCID 20184810[Bis(4-dimethylaminophenyl)(4-methylphenylsulfonyl)]methane

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following a procedure similar to that described in Example 6 above substituting for ethyl alcohol and methanesulfonic acid the appropriate reaction medium and the appropriate catalyst listed in Examples 83-109 of Table B hereinbelow, 4-dimethylaminobenzaldehyde, N,N-dimethylaniline and sodium p-toluenesulfinate were interacted at the indicated temperature to obtain a methane of Formula XV wherein R=4--CH3 ; R5 =H, R6 =N(CH3)2 ; Q=4--(CH3)2NC6H4. A toluene or acetone solution of the product from Examples 83-109 contacted with silica gel developed a blue colored image.

Sources & evidence

ORD record
ord-6913ea75027743ebba81ddc92c9c816a
Source dataset
uspto-grants-1985_01
Patent number
US04494989

Reaction notes

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