4-Methyl-N-(3,4,5-trimethoxybenzyl)aniline → 4-(Methylsulfanyl)-N-[(3,4,5-trimethoxyphenyl)methyl]aniline

HRID 1647302Notes

Reaction equation

HRID 1647302 reaction equation
[CH3:1][S:2][C:3]1[CH:22]=[CH:21][C:6]([N:7]=[CH:8][C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)=[CH:5][CH:4]=1.[BH4-].[Na+].CC1C=CC(NCC2C=C(OC)C(OC)=C(OC)C=2)=CC=1>>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([NH:7][CH2:8][C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)=[CH:21][CH:22]=1

Participants

4

Reactant 3

HCID 3737984-Methyl-N-(3,4,5-trimethoxybenzyl)anilineHCID 4311764Sodium borohydrideHCID 15657370HCID 15657370, compound

Product 1

HCID 3738084-(Methylsulfanyl)-N-[(3,4,5-trimethoxyphenyl)methyl]anilineYield 94.9%

Procedure

From 108e (11.0 g, 35.0 mmol) and NaBH4 (6.6 g, 175 mmol), a similar procedure as described in 109a gave 109e (10.6 g, 94.9%) as an oil: 1H NMR (200 MHz, DMSO-d6) δ7.07 (d, J=8 Hz, 2H), 6.67 (s, 2H), 6.57 (d, J=8 Hz, 2H), 6.23 (t, J=6 Hz, 1H), 4.10, (d, J=6 Hz, 2H), 3.73 (s, 6H), 3.62 (s, 3H), 2.31 (s, 3H). EIMS m/e 319 (M+, 69).

Sources & evidence

ORD record
ord-fba63db1968c4ddca27f98a446829a40
Source dataset
uspto-grants-1995_07
Patent number
US05430062

Reaction notes

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