Thiophenol → HCID 22506599, compound

HRID 1372837Notes

Reaction equation

HRID 1372837 reaction equation
[CH2:1]([O:3][P:4]([N:9]1[CH2:22][CH2:21][N:20](S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][N:12]([S:35]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[N+:44]([O-:46])=[O:45])(=[O:37])=[O:36])[CH2:11][CH2:10]1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].C([O-])([O-])=O.[K+].[K+].C1(S)C=CC=CC=1>CN(C=O)C>[CH2:7]([O:6][P:4]([N:9]1[CH2:10][CH2:11][N:12]([S:35]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[N+:44]([O-:46])=[O:45])(=[O:37])=[O:36])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22]1)([O:3][CH2:1][CH3:2])=[O:5])[CH3:8]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 22506603HCID 22506603, compound

Product 1

HCID 22506599HCID 22506599, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 4-diethoxyphosphoryl-1,7-bis(2-nitrobenzenesulfonyl)-1,4,7-triazacyclotetradecane (1.32 g, 1.87 mmol) and K2CO3 (654 mg, 4.73 mmol) in DMF (11 mL) under nitrogen was added dropwise a solution of thiophenol (0.15 mL, 1.46 mmol) in DMF (8 mL) over 1 h. The mixture was stirred for an additional 3 h and then concentrated in vacuo. The residue was partitioned between CHCl3 (50 mL) and H2O (25 mL). The aqueous phase was separated and extracted with CHCl3 (3×20 mL) and the combined organic extracts were dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography on basic alumina (CHCl3 then 3% MeOH/CHCl3) to give the title compound as a yellow oil (178 mg, 23%): 1H NMR (CDCl3) δ 1.31 (t, 6H, J=7.0 Hz), 1.40–1.67 (m, 10H), 2.65 (m, 2H), 2.78 (m, 2H), 3.12 (m, 2H), 3.26–3.37 (m, 4H), 3.48 (m, 2H), 3.97–4.09 (m, 4H), 7.61 (m, 1H), 7.68 (m, 2H), 8.06 (m, 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between CHCl3 (50 mL) and H2O (25 mL)
  3. customThe aqueous phase was separated
  4. extractionextracted with CHCl3 (3×20 mL)
  5. dry with materialthe combined organic extracts were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on basic alumina (CHCl3

Sources & evidence

ORD record
ord-5089caa74d44481995f65069e9ee3c98
Source dataset
uspto-grants-2007_01
Patent number
US07160872B2

Reaction notes

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