1-(Chloromethoxy)-2-methoxyethane → HCID 66937061, compound

HRID 538141Notes

Reaction equation

[Cl:1][C:2]1[C:3]([S:11][C:12]2[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=2)=[CH:4][C:5]2[N:9]=[CH:8][NH:7][C:6]=2[CH:10]=1.CCN(C(C)C)C(C)C.Cl[CH2:29][O:30][CH2:31][CH2:32][O:33][CH3:34]>C1COCC1>[Cl:1][C:2]1[C:3]([S:11][C:12]2[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=2)=[CH:4][C:5]2[N:9]=[CH:8][N:7]([CH2:29][O:30][CH2:31][CH2:32][O:33][CH3:34])[C:6]=2[CH:10]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a cooled solution (0° C.) of 6-chloro-5-m-tolylsulfanyl-1H-benzoimidazole (2.14 g, 7.78 mmol) and THF (39 mL) was added DIPEA (2.71 mL, 15.6 mmol). 1-Chloromethoxy-2-methoxy-ethane (0.977 mL, 8.56 mmol) was added dropwise, and the reaction mixture was allowed to warm to 23° C. over 16 h. The reaction mixture was concentrated. The residue was purified (FCC) (0-100% EtOAc/hexanes) to yield the titled compound (1.89 g, 67%) as a 1:1 mixture of regioisomers. MS (ESI/CI): mass calcd. for C18H19ClN2O2S, 362.1; m/z found, 363.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.95 (s, 1H), 7.92 (s, 1H), 7.88 (s, 1H), 7.64 (s, 1H), 7.59 (s, 1H), 7.41 (s, 1H), 7.22-7.18 (m, 3H), 7.16-7.13 (m, 2H), 7.11-7.05 (m, 3H), 5.56 (s, 2H), 5.47 (s, 2H), 3.57-3.54 (m, 2H), 3.52-3.49 (m, 2H), 3.48-3.45 (m, 2H), 3.44-3.42 (m, 2H), 3.35 (s, 3H), 3.30 (s, 3H), 2.30 (s, 6H).

Workup

concentrationThe reaction mixture was concentrated
customThe residue was purified (FCC) (0-100% EtOAc/hexanes)

Sources & evidence

ORD record: ord-123979741a0c4a3a8fe71618617e5df6
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865713B2

Reaction notes

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