Carbon Dioxide → HCID 15411537, compound

Participants

Reaction Steps

A solution of 1.3 N of n-butyllithium in hexane (0.7 ml) was added to a solution of 220 mg of 6-[(2-methoxyethoxy)methoxy]benzothiazole (obtained as in paragraph 1 above) in 30 ml of tetrahydrofuran at -78° C. cooled by dry ice--acetone. The mixture was added dropwise into a solution of 234 mg of ethyl 4-[(2-methoxyethoxy)methoxy]benzoate (obtained as in paragraph 2 above) in tetrahydrofuran (3 ml) cooled by dry ice--acetone. NH4Cl was added to the reaction mixture and the mixture was extracted with ether. The extracts were washed with water and dried over sodium sulfate. After being concentrated, the residue was recrystallized from ethyl acetate to yield 320 mg of 6-(2-methoxyethoxy)methoxy-2-{4-[(2-methoxyethoxy)methoxy]benzoyl}benzothiazole (Compound 1). mp: 46° C. 1H-NMR(CDCl3): 3.38(s,3H), 3.38(s,3H), 3.58(m,4H), 3.86(m,4H), 5.38(s,4H), 7.18(d,J=8.8 Hz,2H), 7.28(dd,J=9.1,2.2 Hz,1H), 7.67(d,J=2.2 Hz,1H), 8.10(d,J=9.1 Hz,1H), 8.59(d,J=8.8 Hz,2H) IR(KBr) cm-1 : 2877, 1598, 1488, 1214, 1117, 987 MS m/z: 447(M+), 89, 59 Elementary analysis (C22H25NO7S): Calculated (C=59.05,H=5.63,N=3.13); Found (C=59.15,H=5.58,N=2.93)

Provenance & Evidence