2-Furanmethanethiol → HCID 10742479, compound

HRID 248832

Reaction equation

HRID 248832 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[O:6][C:7]3[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=3[CH2:9][N:10]([C:11]([NH:13][CH2:14][C:15](=[O:18])[CH:16]=[CH2:17])=[O:12])[C:4]=2[CH:3]=1.[CH2:25]([SH:31])[C:26]1[O:30][CH:29]=[CH:28][CH:27]=1.N1CCCCC1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>C(Cl)Cl.CO.CCOC(C)=O>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[O:6][C:7]3[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=3[CH2:9][N:10]([C:11]([NH:13][CH2:14][C:15](=[O:18])[CH2:16][CH2:17][S:31][CH2:25][C:26]3[O:30][CH:29]=[CH:28][CH:27]=3)=[O:12])[C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 73632-FuranmethanethiolHCID 8082PiperidineHCID 66854Benzyltrimethylammonium hydroxideHCID 10831197HCID 10831197, compound

Product 1

HCID 10742479HCID 10742479, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 8-chloro-N-(2-oxo-3-butenyl)dibenz[b,f][1,4]oxazepin-10(11H)-carboxamide (0.75 gram), furfuryl mercaptan (0.23 mL), piperidine (0.069 mL), and N-benzyltrimethylammonium hydroxide (0.069 mL) in methylene chloride (12 mL) and methanol (3 mL) was stirred at room temperature for 6 hours. The reaction was diluted with methylene chloride (75 mL), washed with 75 mL each of 1N HCl (two times), water, saturated aqueous sodium bicarbonate, and brine, dried over MgSO4, and evaporated in vacuo. The crude product was purified by flash chromatography through silica gel 60 (350 mL) using 95:5 methylene chloride: ethyl acetate to yield a colorless oil. Analysis calculated for C23H21ClN2O4S×0.1 EtOAc: C, 60.34; H, 4.72; N, 6.01; Cl, 7.61; S, 6.88. Found: C, 59.94; H, 4.84; N, 5.87; Cl, 8.13; S, 6.65.

Workup

  1. washwashed with 75 mL each of 1N HCl (two times), water, saturated aqueous sodium bicarbonate, and brine
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. customThe crude product was purified by flash chromatography through silica gel 60 (350 mL)
  5. customethyl acetate to yield a colorless oil

Sources & evidence

ORD record
ord-4f1d21f2d9974500b6b242551c69a2b2
Source dataset
uspto-grants-1993_05
Patent number
US05212169

Linked notes

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