Hydrogen Sulfide → N-acetylformyl,N-(4-chlorophenyl)valine

HRID 648268Notes

Reaction equation

HRID 648268 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C@H:9]([C:13]([OH:15])=[O:14])[CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1.N([CH2:23][CH2:24][OH:25])(CCO)CCO.S.CN([CH:30]=[O:31])C>>[C:24]([C:30]([N:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C@H:9]([C:13]([OH:15])=[O:14])[CH:10]([CH3:12])[CH3:11])=[O:31])(=[O:25])[CH3:23]

Participants

5

Reactant 4

HCID 402Hydrogen SulfideHCID 6228DimethylformamideHCID 7618TriethanolamineHCID 13796078N-(p-chlorophenyl)valine

Product 1

HCID 57070001N-acetylformyl,N-(4-chlorophenyl)valine

Procedure

To a mixture of the α-cyano-m-phenoxybenzyl ester of N-(4-chlorophenyl)valine (0.79 g) and about 20 ml of dry DMF is added about one ml of triethanolamine at RT. Into the mixture is slowly bubbled H2S gas for about 3 hours. The reaction is then stirred overnight. The reaction is worked up by partition with ether/water. The organic phase is washed with brine (3×), dried over sodium sulfate, filtered and evaporated. The residue is plated on a prep. TLC plate eluting with 20% ethyl acetate/hexane to yield the desired thioamide, MS m/e 181.9 (100), IR (film) 3180 cm-1 (NH) and 1740 cm-1 (C=O). ##STR25##

Workup

  1. customfor about 3 hours
  2. customby partition with ether/water
  3. washThe organic phase is washed with brine (3×)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. washTLC plate eluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-1d325316910b413d898142337f95e6b2
Source dataset
uspto-grants-1983_10
Patent number
US04411912

Reaction notes

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