4-Ethoxyaniline → HCID 178466744, compound

HRID 901911Notes

Reaction equation

[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[CH2:11]([O:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1)[CH3:12]>>[CH2:11]([O:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][C:7]([C:6]2[CH:9]=[CH:10][C:3]([S:2][CH3:1])=[CH:4][CH:5]=2)=[NH:8])=[CH:16][CH:15]=1)[CH3:12]

Participants

Reactant 2

HCID 90764-Ethoxyaniline

HCID 5909604-(Methylthio)benzonitrile

Product 1

HCID 178466744HCID 178466744, compoundYield 61%

Procedure

The title compound was prepared from 4-methylthiobenzonitrile (10.87 g, 73 mmol) and 4-ethoxyaniline (10 g, 73 mmol) by following the procedure described in preparation 10 (12.7 g, yield 61%, purity 96.27% by HPLC). 1H-NMR (CDCl3):δ 1.39-1.43 (t, 3H), 2.51 (s, 3H), 3.99-4.04 (q, 2H), 4.75 (bs, 2H, D2O exchangeable), 6.90 (s, 4H), 7.26-7.29 (m, 2H), 7.77-7.79 (d, 2H). MS m/z:287.2 (M+).

Workup

customdescribed in preparation 10 (12.7 g, yield 61%, purity 96.27% by HPLC)

Sources & evidence

ORD record: ord-585e018735a04581bbc7f9d15435b8a1
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365069B2

Reaction notes

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