Chloroform → HCID 54221449, compound

Participants

Role	Name	HCID	Charge
Reactant	Chloroform	HCID 6212	—
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	2-Chloro-5-(chloromethyl)thiophene	HCID 583079	—
Reactant	2-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]-2H-1,4-benzoxazin-3(4H)-one	HCID 12048020	—
Solvent	Water	HCID 962	—
Solvent	Hexane	HCID 8058	—
Product	HCID 54221449	HCID 54221449	—

Reaction Steps

Prepared from 2-(2-tert-butyldimethylsiloxyethyl)-3,4-dihydro-3-oxo-2H-1,4-benzoxazine by Methods F and G, alkylating with 5-chloro-2-(chloromethyl)thiophene and was isolated in 83% overall yield as a light yellow viscous oil after flash chromatography using 30-50% EtOAc in hexane; IR (CHCl3) 3418, 2943, 1677, 1500, 1400, 1278, 1062, 750 cm-1 ; 1H NMR (CDCl3) δ 2.11-2.32 (m, 3H), 3.89 (q, J=5.4 Hz, 2H), 4.78 (dd, J=7.6, 5.5 Hz, 1H), 5.15 (ABq, JAB =16.0 Hz, 2H), 6.74 (d, J=3.7 Hz, 1H), 6.84 (d, J=3.7 Hz, 1H), 7.01-7.08 (m, 4H); MH+ at m/z=324; Anal. Calc'd for C15H14ClNO3S.0.25 H2O: C, 54.88; H, 4.45; N, 4.27; S, 9.77. Found: C, 54.86; H, 4.41; N, 4.04; S, 9.87.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05854242
Source dataset	uspto-grants-1998_12
ORD ID	ord-23d682a80909426f8e1710079d168abb
Source note	uspto-grants-1998_12