Triethylamine → HCID 57662051, compound

HRID 1665275Notes

Reaction equation

HRID 1665275 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([O:11][C:10]3[C:12]4[C:17]([C:18](=[O:21])[C:19](=[O:20])[C:9]=3[S:8][CH2:7]2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH2:3][CH2:2]1.[O:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[C:27](Cl)=[O:28].C(N(CC)CC)C>ClCCl>[O:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[C:27]([N:1]1[CH2:2][CH2:3][C:4]2([O:11][C:10]3[C:12]4[C:17]([C:18](=[O:21])[C:19](=[O:20])[C:9]=3[S:8][CH2:7]2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH2:5][CH2:6]1)=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 57661820Spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Product 1

HCID 57662051HCID 57662051, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of spiro[naphtho[1,2-b][1,4]oxathiine-2,4′-piperidine]-5,6-dione (0.1 g, 0.33 mmol) in dichloromethane (3.0 mL) was added 2-furoyl chloride (0.050 g, 0.40 mmol) followed by triethylamine (0.114 mL, 0.79 mmol). The reaction mixture was stirred for 1 h at room temperature. The organic layer was separated, washed with water (2.0 mL), dried with sodium sulfate and concentrated under vacuum. The crude product was crystallized from EtOAc and hexanes to give the desired product as a purple solid (0.08 g, 61%). M.p.=165° C.; 400 MHz 1H NMR (DMSO-d6) δ 7.89-7.85 (m, 3H), 7.78 (t, 1H), 7.57 (t, 1H), 7.02 (d, J=3.6 Hz, 1H), 6.63 (d, J=3.6 Hz, 1H), 4.24 (d, 2H), 3.13 (s, 2H), 2.15 (brs, 2H), 2.08 (brs, 2H), 1.95 (m, 2H); LCMS: 396 [M+H].

Workup

  1. customThe organic layer was separated
  2. washwashed with water (2.0 mL)
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe crude product was crystallized from EtOAc and hexanes

Sources & evidence

ORD record
ord-9fc043656bf4422794dbe7ed407078cb
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

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