4-Methyl-N-[(3,4,5-trimethoxyphenyl)methyl]aniline--hydrogen chloride (1/1) → 4-(Methylsulfanyl)-N-[(3,4,5-trimethoxyphenyl)methyl]aniline--hydrogen chloride (1/1)

HRID 1647307Notes

Reaction equation

HRID 1647307 reaction equation
[CH3:1][S:2][C:3]1[CH:22]=[CH:21][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:5][CH:4]=1.[ClH:23].CC1C=CC(NCC2C=C(OC)C(OC)=C(OC)C=2)=CC=1>>[ClH:23].[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

3

Reactant 2

HCID 3737994-Methyl-N-[(3,4,5-trimethoxyphenyl)methyl]aniline--hydrogen chloride (1/1)HCID 3738084-(Methylsulfanyl)-N-[(3,4,5-trimethoxyphenyl)methyl]aniline

Product 1

HCID 3738094-(Methylsulfanyl)-N-[(3,4,5-trimethoxyphenyl)methyl]aniline--hydrogen chloride (1/1)Yield 53.9%

Procedure

From 109e (3.0 g, 9.4 mmol), a similar procedure as described for 110a gave 110e (1.80 g, 53.9%) as yellow crystals: mp 194°-6° C. after recrystallization from ethanol:methanol:water. 1H NMR (200 MHz, DMSO-d6) δ7.23 (d, J=8 Hz, 2H), 7.07 (d, J=8 Hz, 2H), 6.83 (s, 2H), 4.30 (s, 2H), 3.73 (s, 6H), 3.62 (s, 3H), 3.62 (s, 3H), 2.40 (s, 3H). Anal (C17H22ClNO3S) C, H, N.

Sources & evidence

ORD record
ord-468f2ea4153e4d9ea0f79bdba8b44819
Source dataset
uspto-grants-1995_07
Patent number
US05430062

Reaction notes

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