Ethanethiol → HCID 22393124, compound

HRID 609553Notes

Reaction equation

[CH2:1]([C:5]1([CH2:26][CH3:27])[CH2:11][N:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[CH:18]=[C:19]([O:22]C)[CH:20]=[CH:21][C:8]=2[S:7](=[O:25])(=[O:24])[CH2:6]1)[CH2:2][CH2:3][CH3:4].[Br-].[Al+3].[Br-].[Br-].C(S)C>>[CH2:1]([C:5]1([CH2:26][CH3:27])[CH2:11][N:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[CH:18]=[C:19]([OH:22])[CH:20]=[CH:21][C:8]=2[S:7](=[O:24])(=[O:25])[CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

Reactant 3

HCID 6343Ethanethiol

HCID 166749Bromhydrol

HCID 19599342HCID 19599342, compound

Product 1

HCID 22393124HCID 22393124, compoundYield 89%

Procedure

The compound of Example 26 (1.05 g, 2.71 mmol) was treated with aluminum bromide and ethanethiol according to the procedure for Example 18 giving the title product (0.90 g, 89%). 1H NMR (DMSO-d6) δ 9.99 (s, 1H); 7.27-6.74 (m, 8H); 3.61 (br s, 2H), 3.20 (s, 2H); 1.50-1.00 (m, 8H); 0.73 (m, 6H). MS Da/e=374 (MH+). Calcd for C21H27NSO3 ×0.25 H2O: C, 66.73; H, 7.33, N, 3.71, S, 8.48. Found: C, 66.67; H, 7.32; N, 3.67; S, 8.49.

Sources & evidence

ORD record: ord-3694e69d327b4114a8326ce3fd3b10c4
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05998400

Reaction notes

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