Dimethyl Sulfoxide → HCID 86606155, compound

HRID 643227Notes

Reaction equation

[CH3:1][C:2]1C(=O)[N:6]([C:9]2[C:10](=[O:27])[O:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([N:19]2[C:23](=[O:24])[C:22]([CH3:25])=[CH:21][C:20]2=O)=[CH:14][CH:13]=3)[C:4](=[O:5])[CH:3]=1.[CH2:28]([SH:30])[CH3:29].C[S:32]([CH3:34])=O>>[CH2:2]([CH:3]1[C:4](=[O:5])[N:6]([C:9]2[C:10](=[O:27])[O:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([N:19]2[C:23](=[O:24])[CH:22]([CH2:21][CH3:20])[CH2:25][C:34]2=[S:32])=[CH:14][CH:13]=3)[C:28](=[S:30])[CH2:29]1)[CH3:1]

Participants

Reactant 3

HCID 679Dimethyl Sulfoxide

HCID 6343Ethanethiol

HCID 86606157HCID 86606157, compound

Product 1

HCID 86606155HCID 86606155, compoundYield 84%

Procedure

The reaction of 44 mg (0.12 mmol) of compound 6 in 3 mL dry DMSO with 27 μL ethanethiol (0.36 mmol) was carried out according to the same protocol used to obtain compound 7, giving compound 9 in 84% yield (49 mg, 0.1 mmol). FTIR (KBr) (cm−1): 1720, 1620, 600. 1H-NMR (CDCl3): δ (ppm) 8.21 (s, 1H), 7.57 (d, J=2.53 Hz, 1H), 7.39 (dd, J=8.47 Hz, J=2.67 Hz, 1H), 7.26 (d, J=8.35 Hz, 1H), 3.84 (s, 1H), 3.12 (s, 1H), 3.07 (s, 1H, 2.83 (m, 4H), 1.93 (d, J=7.08 Hz, 3H), 1.90 (d, J=7.25 Hz, 3H), 1.30 (t, J=7.28 Hz, 6H). 13C-NMR (DMSO-d6): δ (ppm) 175.04, 172.32, 167.92, 156.34, 150.73, 137.21, 129.87, 128.65, 124.34, 118.03, 117.04, 38.53, 34.29, 26.02, 20.68, 14.27, 11.67. HRMS expected for C23H24N2O6S2: 488.107580; found: 488.107213.

Sources & evidence

ORD record: ord-93461353037b47c2b2e577c896087b3b
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700375B2

Reaction notes

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