Hydrogen Sulfide → HCID 13647287, compound

HRID 1981833Notes

Reaction equation

HRID 1981833 reaction equation
[SH2:1].[CH3:2][C:3]1([C:20]#[N:21])[CH2:7][CH2:6][C:5]([CH2:18][CH3:19])([CH2:8][O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[O:4]1>N(CCO)(CCO)CCO.C(O)C>[CH2:18]([C:5]1([CH2:8][O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[O:4][C:3]([CH3:2])([C:20](=[S:1])[NH2:21])[CH2:7][CH2:6]1)[CH3:19]

Participants

5

Reactant 2

HCID 402Hydrogen SulfideHCID 13647283HCID 13647283, compound

Product 1

HCID 13647287HCID 13647287, compound

Reagents, catalysts & solvents 2

HCID 7618TriethanolamineCatalystHCID 702EthanolSolvent

Procedure

Excess hydrogen sulfide was condensed into a stainless steel bomb containing 2.94 g of the chromatographically purified trans-nitrile, tetrahydro-2-methyl-5-ethyl-5-[(2-chlorophenylmethoxy)methyl]-2-furancarbonitrile, (ca>9:1 trans-cis by proton NMR), 10 ml ethanol, and 0.15 g triethanolamine catalyst. The sealed bomb was kept at 55±3° C. for 6 hours during which time the internal pressure rose to 350 psi. After cooling, the reaction mixture was concentrated on a rotary evaporator. The residue was purified by dry column chromatography on silica gel using 96.4 hexane:tetrahydrofuran as eluent. The white cyrstalline desired product weighed 1.10 g, mp 78°-80° C.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated on a rotary evaporator
  3. customThe residue was purified
  4. customby dry column chromatography on silica gel using 96.4 hexane

Sources & evidence

ORD record
ord-d371f603823b47e1b8acd3723c527b57
Source dataset
uspto-grants-1986_06
Patent number
US04594094

Reaction notes

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