Tetrahydrofuran → HCID 18939905, compound

HRID 355588Notes

Reaction equation

HRID 355588 reaction equation
[NH:1]=[C:2]1[N:6]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([C:15]([F:18])([F:17])[F:16])[CH:8]=2)[C:5](=[S:19])[N:4]([CH3:20])[C:3]1([CH3:22])[CH3:21].[O:23]1[CH2:27]CC[CH2:24]1>C(N(CC)CC)C>[CH3:21][C:3]1([CH3:22])[C:2](=[NH:1])[N:6]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([C:15]([F:17])([F:16])[F:18])[CH:8]=2)[C:5](=[S:19])[N:4]1[CH2:20][CH2:24][OH:23].[C:11]([C:10]1[CH:9]=[CH:8][C:7]([NH:6][C:5]([N:4]2[CH2:20][CH2:27][O:23][C:3]2([CH3:21])[CH3:22])=[S:19])=[C:14]([C:15]([F:18])([F:17])[F:16])[CH:13]=1)#[N:12]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 22116939HCID 22116939, compound

Product 2

HCID 18939905HCID 18939905, compoundHCID 22116927HCID 22116927, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 1.18 g of the said mixture, 2.11 g of the isothiocyanate of Example 11 and 20 ml of tetrahydrofuran and 0.5 ml of triethylamine was refluxed for 30 minutes and then evaporated to dryness. The residue was chromatographed on silica and eluted with a 95-5 methylene chloride-acetone mixture to obtain 1.26 g of the desired product and 686 mg of N-(4-cyano-2-trifluoromethyl-phenyl)-2,2-dimethyl-3-oxazolidine carbothioamide. The 686 mg were dissolved in 10 ml of ethyl acetate and after the addition of 30 ml of cyclohexane, the mixture was concentrated to 4 ml and vacuum filtered and dried to obtain another 518 mg of product. The raw product was dissolved in 20 ml of isopropanol and the solution was concentrated to 5 ml, vacuum filtered and dried to obtain 1.04 g of the desired product melting at 181° C.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. customevaporated to dryness
  3. customThe residue was chromatographed on silica
  4. washeluted with a 95-5 methylene chloride-acetone mixture

Sources & evidence

ORD record
ord-66ffb88999154183b89a0d9c95806366
Source dataset
uspto-grants-1998_11
Patent number
USRE035956

Reaction notes

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