Hydrochloric Acid → 4-(4H-benzo[d][1,3]oxathiin-2-yl)benzonitrile

HRID 1876292Notes

Reaction equation

HRID 1876292 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)=[O:2].[SH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18]O.Cl>ClCCl>[S:11]1[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:18][O:2][CH:1]1[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 660424-CyanobenzaldehydeHCID 1382782-Mercaptobenzenemethanol

Product 1

HCID 441366804-(4H-benzo[d][1,3]oxathiin-2-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the same procedure as outlined in Example 1 step b), 4-formylbenzonitrile (0.78 g, 5.95 mmol) and (2-mercaptophenyl)methanol (1 g, 7.14 mmol) in dichloromethane (30 ml) were treated with hydrogen chloride gas. After workup and chromatography, as in example 1 step b), the subtitle compound was obtained (1.12 g, 75%) as a white solid. 1H NMR (300 MHz, CDCl3, ppm) δ 5.10 (s, 2H); 6.15 (s, 1H); 7.04-7.21 (m, 4H); 7.59-7.68 (m, 4H); 13C NMR (75 MHz, CDCl3, ppm) δ 70.2; 81.7; 112.8; 118.6; 125.6; 126.1; 127.1; 127.6; 127.7; 129.9; 132.0; 132.6; 143.4; MS calculated for C15H11NOS+H 254 observed 254.

Sources & evidence

ORD record
ord-944ee69712564353b67863bfcdae32e1
Source dataset
uspto-grants-2012_11
Patent number
US08309598B2

Reaction notes

Loading…