Triethylamine → HCID 67330823, compound

HRID 1258381Notes

Reaction equation

HRID 1258381 reaction equation
C(N(CC)CC)C.[O:8]=[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=O)[CH:11]=[C:10]1[O:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].[S:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[S:34]([NH2:37])(=[O:36])=[O:35]>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[C:25]([O:24][C:22](=[O:23])[CH2:21][O:20][C:10]1[C:9](=[O:8])[C:18]2[C:13]([C:12](=[N:37][S:34]([C:30]3[S:29][CH:33]=[CH:32][CH:31]=3)(=[O:36])=[O:35])[CH:11]=1)=[CH:14][CH:15]=[CH:16][CH:17]=2)([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 728812-ThiophenesulfonamideHCID 58398217HCID 58398217, compound

Product 1

HCID 67330823HCID 67330823, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

triethyl amine (0.12 ml, 0.88 mmol) was added in the mixture of tert-Butyl 2-(1,4-dioxo-1,4-dihydronaphthalen-2-yloxy)acetate (7c, 0.115 g, 0.4 mmol) and thiophene-2-sulfonamide (0.078 g, 0.48 mmol) in anhydrous DCM (4 ml), followed by adding TiCl4.2THF. The reaction mixture was heated with μW at 60° C. for 20 min. and poured into EtOAC, then filtered with celite. The filtrate was concentrated under reduce pressure and purified by flash chromatography to give compound 8d as a yellow solid, 22%, m.p.=153-155° C.

Workup

  1. additionpoured into EtOAC
  2. filtrationfiltered with celite
  3. concentrationThe filtrate was concentrated
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-325da5ce4fc94852b37546131c1e69b9
Source dataset
uspto-grants-2013_06
Patent number
US08466157B2

Reaction notes

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