Sulfuryl chloride → HCID 10227835, compound

HRID 1278833Notes

Reaction equation

HRID 1278833 reaction equation
[Br:1][C:2]1[C:11]2[S:12][C:13]([CH3:16])=[C:14]([CH3:15])[C:10]=2[C:9]([C:17]2[CH:22]=[C:21]([CH3:23])[C:20]([O:24][CH3:25])=[C:19]([CH3:26])[CH:18]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.S(Cl)(Cl)(=O)=O.C(N(C(C)C)CC)(C)C.[C:41]([O-:44])(=[O:43])[CH3:42].[Na+]>C(OCC)C.CN(C)C=O.C(Cl)Cl>[C:41]([O:44][CH2:16][C:13]1[S:12][C:11]2[C:2]([Br:1])=[C:3]3[C:8](=[C:9]([C:17]4[CH:22]=[C:21]([CH3:23])[C:20]([O:24][CH3:25])=[C:19]([CH3:26])[CH:18]=4)[C:10]=2[C:14]=1[CH3:15])[CH:7]=[CH:6][CH:5]=[CH:4]3)(=[O:43])[CH3:42]

Participants

8

Reactant 4

HCID 24648Sulfuryl chlorideHCID 81531DiisopropylethylamineHCID 517045Sodium AcetateHCID 18430695HCID 18430695, compound

Product 1

HCID 10227835HCID 10227835, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2,6-dimethyl-anisole (2.0 g, 4.7 mmol), sulfuryl chloride (0.42 mL, 5.3 mmol), diisopropylethylamine (0.90 mL, 5.2 mmol), and anhydrous methylene chloride (24 mL) was stirred at 0° C. for approximately 2 h. The crude reaction mixture was then diluted with diethyl ether, washed twice with water, once with brine, and then dried (Na2SO4). Concentration under reduced pressure gave a residue, which was immediately treated with sodium acetate (1.2 g, 14.6 mmol) and N,N-dimethylformamide (16.8 mL). After 24 h the reaction mixture was diluted with diethyl ether, washed three times with water, once with brine, and then dried (Na2SO4). Concentration under reduced pressure gave a residue, which was chromatographed with hexane/ethyl acetate to give the title compound as a yellow foam (0.36 g, 27%): (DMSO-d6): δ 8.41 (s, 1H), 8.21 (d, J=9 Hz, 1H), 7.68 (ddd, J=2, 6, 8 Hz, 1H), 7.57-7.45 (m, 2H), 7.05 (s, 2H), 3.78 (s, 3H), 2.30 (s, 6H), 2.08 (s, 3H), 1.68 (s, 3H); MS(EI): [M+], 1 bromine isotope pattern, 482/484; Anal. Calc. for C25H23BrO3S: C, 62.11, H, 4.80, N, 0.00. Found: C, 61.86, H, 4.75, N, 0.04.

Workup

  1. customThe crude reaction mixture
  2. washwashed twice with water, once with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationConcentration under reduced pressure
  5. customgave a residue, which
  6. washwashed three times with water
  7. dry with materialonce with brine, and then dried (Na2SO4)
  8. concentrationConcentration under reduced pressure
  9. customgave a residue, which
  10. customwas chromatographed with hexane/ethyl acetate

Sources & evidence

ORD record
ord-06313ecf95fb4541bc130d3986e5858e
Source dataset
uspto-grants-2002_09
Patent number
US06444670B2

Reaction notes

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