4-(Dimethylamino)benzene-1-thiol → trans-2-[-3-n-Propylsulfonyl-4-{2-(4-Dimethylaminophenylthio)ethoxy}-5-methoxyphenyl}-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran

HRID 1196709Notes

Reaction equation

HRID 1196709 reaction equation
[CH2:1]([S:4]([C:7]1[CH:8]=[C:9]([C@H:19]2[CH2:23][CH2:22][C@H:21]([C:24]3[CH:29]=[C:28]([O:30][CH3:31])[C:27]([O:32][CH3:33])=[C:26]([O:34][CH3:35])[CH:25]=3)[O:20]2)[CH:10]=[C:11]([O:17][CH3:18])[C:12]=1[O:13][CH2:14][CH2:15]Br)(=[O:6])=[O:5])[CH2:2][CH3:3].[CH3:36][N:37]([CH3:45])[C:38]1[CH:43]=[CH:42][C:41]([SH:44])=[CH:40][CH:39]=1.[H-].[Na+]>CN(C=O)C>[CH2:1]([S:4]([C:7]1[CH:8]=[C:9]([C@H:19]2[CH2:23][CH2:22][C@H:21]([C:24]3[CH:29]=[C:28]([O:30][CH3:31])[C:27]([O:32][CH3:33])=[C:26]([O:34][CH3:35])[CH:25]=3)[O:20]2)[CH:10]=[C:11]([O:17][CH3:18])[C:12]=1[O:13][CH2:14][CH2:15][S:44][C:41]1[CH:42]=[CH:43][C:38]([N:37]([CH3:45])[CH3:36])=[CH:39][CH:40]=1)(=[O:6])=[O:5])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 210614-(Dimethylamino)benzene-1-thiolHCID 24758Sodium hydrideHCID 67907009trans-2-[3-n-Propylsulfonyl-4-(2-bromoethoxy)-5-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran

Product 1

HCID 67906668trans-2-[-3-n-Propylsulfonyl-4-{2-(4-Dimethylaminophenylthio)ethoxy}-5-methoxyphenyl}-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Trans-2-[3-n-propylsulfonyl-4-(2-bromoethoxy)-5-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran (100 mg) (Step 30G) was added to a stirred solution of 4-dimethylaminothiophenol (76 mg, 0.5 mmol) and sodium hydride (56%; 20 mg, 0.5 mmol) in DMF (1 mL). The reaction mixture was stirred at room temperature for 20 min and partitioned between ethyl ether and water. The organic layer was separated, dried, and evaporated to a crystalline mass. Recrystallized from ethyl ether-hexane gave pure product: mp 113°-115° C.; NMR (CDCl3) δ 1.0 (t, CH2CH2CH3), 1.70 (m, CH2CH2CH3), 2.0 & 2.49 (2 m, H-3 & H-4), 3.0 [m, (CH3)2N], 3.4 (m, CH2CH2CH3), 3.84 3.88 & 3.9 (3 s, 3 OCH3), 4.30 (t, SCH2CH2O), 5.22 (m, H-2 & H-5), 6.62 (s, C5ArH), 7.23 & 7.47 (2 d, J=1.5 Hz, C2ArH), 7.42 (m, ArH).

Workup

  1. custompartitioned between ethyl ether and water
  2. customThe organic layer was separated
  3. customdried
  4. customevaporated to a crystalline mass
  5. customRecrystallized from ethyl ether-hexane
  6. customgave pure product

Sources & evidence

ORD record
ord-e3856f55dffa4f5781f0429c8c010f36
Source dataset
uspto-grants-1992_05
Patent number
US05114961

Reaction notes

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