4-Ethylaniline → HCID 178436605, compound

HRID 901905Notes

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]([C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1)[CH3:12]>>[CH2:11]([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)[CH3:12]

Participants

Reactant 2

HCID 115044-Ethylaniline

HCID 5909604-(Methylthio)benzonitrile

Product 1

HCID 178436605HCID 178436605, compoundYield 81.1%

Procedure

The title compound was prepared from 4-methylthiobenzonitrile (1.23 g, 8.2 mmol) and 4-ethylaniline (1 g, 8.2 mmol) by following the procedure described in preparation 10 (1.81 g, yield 81.1%, mp 156-158° C., purity 98.6% by HPLC). 1H-NMR (CDCl3): δ 1.22-1.26 (t, 3H), 2.51 (s, 3H), 2.60-2.66 (q, 2H), 4.70 (bs, 2H, D2O exchangeable), 6.89-6.91 (d, 2H), 7.17-7.19 (d, 2H), 7.26-7.29 (m, 2H), 7.79-7.81 (d, 2H). MS m/z:271.3 (M+).

Workup

customdescribed in preparation 10 (1.81 g, yield 81.1%, mp 156-158° C., purity 98.6% by HPLC)

Sources & evidence

ORD record: ord-d391ee047dc04c44ac0bb32ac5d2bedc
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365069B2

Reaction notes

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