Lawesson's reagent → HCID 87209109, compound

HRID 1364106Notes

Reaction equation

HRID 1364106 reaction equation
[CH3:1][C:2]1([CH3:29])[CH2:27][C:6]2[N:7]=[C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH:11]3[CH2:16][C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([CH3:26])[CH:24]=4)[NH:19][CH:18]=3)[S:9][C:5]=2[C:4](=O)[CH2:3]1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:39]2)=CC=1.C([O-])(O)=O.[Na+]>C1COCC1>[CH3:1][C:2]1([CH3:29])[CH2:27][C:6]2[N:7]=[C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH:11]3[CH2:16][C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([CH3:26])[CH:24]=4)[NH:19][CH:18]=3)[S:9][C:5]=2[C:4](=[S:39])[CH2:3]1

Participants

5

Reactant 3

HCID 87949Lawesson's reagentHCID 516892Sodium BicarbonateHCID 11998688HCID 11998688, compound

Product 1

HCID 87209109HCID 87209109, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of Example 21 (0.06 g, 0.15 mmol) in THF (10 mL) at r.t. was added 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulphide (0.06 g, 0.15 mmol). The reaction mixture was stirred for 2 h and then poured into aqueous sat. NaHCO3 solution (50 mL) and extracted with DCM (2×50 mL). The combined organic fractions were dried over MgSO4, filtered and the solvent removed in vacuo to give the title compound (0.02 g, 35%) as an orange solid. δH (DMSO-d6) 10.33 (1H, br. s), 7.63 (1H, d, J 8.0 Hz), 7.10 (2H, m), 6.86 (1H, d, J 8.0 Hz), 4.16 (1H, br. s), 3.98 (1H, d, J 8.0 Hz), 3.73 (2H, m), 3.57 (3H, m), 3.31 (1H, m), 3.01 (1H, m), 2.74 (2H, s), 2.57 (2H, d, J 5.6 Hz), 2.40 (3H, s), 1.04 (6H, s). LCMS (ES+) 426.9 (M+H)+.

Workup

  1. extractionextracted with DCM (2×50 mL)
  2. dry with materialThe combined organic fractions were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-76dfca9df4e64f58ab007001f4539572
Source dataset
uspto-grants-2011_02
Patent number
US07888344B2

Reaction notes

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