P-Anisidine → HCID 178492294, compound

HRID 901907Notes

Reaction equation

HRID 901907 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[CH3:11][O:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1.[K+].[Br-]>>[CH3:11][O:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][C:7]([C:6]2[CH:9]=[CH:10][C:3]([S:2][CH3:1])=[CH:4][CH:5]=2)=[NH:8])=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 7732P-AnisidineHCID 253877Potassium BromideHCID 5909604-(Methylthio)benzonitrile

Product 1

HCID 178492294HCID 178492294, compoundYield 76.84%

Procedure

The title compound was prepared from 4-methylthiobenzonitrile (12.11 g, 81 mmol) and 4-methoxyaniline (10 g, 81 mmol) by following the procedure described in preparation 10 (17 g, yield 76.84%, mp 166-168° C., purity 97.25% by HPLC). 1H-NMR (CDCl3):δ 2.51 (s, 3H), 3.80 (s, 3H), 4.80 (bs, 2H, D2O exchangeable), 6.91 (s, 4H), 7.26-7.29 (m, 2H), 7.78-7.8 (d, 2H). IR (KBr) cm−1: 3461, 3320, 2949, 2922, 2829, 1615. MS m/z:273.1 (M+).

Workup

  1. customdescribed in preparation 10 (17 g, yield 76.84%, mp 166-168° C., purity 97.25% by HPLC)

Sources & evidence

ORD record
ord-bfc07f67acd54fde9fceba119d87049a
Source dataset
uspto-grants-2008_04
Patent number
US07365069B2

Reaction notes

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