Hydrogen Sulfide → HCID 10379787, compound

HRID 1029546Notes

Reaction equation

HRID 1029546 reaction equation
[SH2:1].[CH3:2][C:3]([C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:15]=1[OH:16])[O:9][CH2:10][C:11]#[N:12])([CH3:5])[CH3:4].C(N(CC)CC)C>N1C=CC=CC=1.CCOCC>[CH3:18][C:17]([C:14]1[CH:13]=[C:8]([CH:7]=[C:6]([C:3]([CH3:2])([CH3:4])[CH3:5])[C:15]=1[OH:16])[O:9][CH2:10][C:11](=[S:1])[NH2:12])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 10445384HCID 10445384, compound

Product 1

HCID 10379787HCID 10379787, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

Hydrogen sulfide gas is bubbled for 30 minutes into a solution of [3,5-bis(1,1-dimethylethyl)-4-hydroxyphenoxy] acetonitrile (1.16 g, 4.44 mmol) and triethylamine (0.68 mL, 4.88 mmol) in pyridine (4.5 mL). The reaction mixture is diluted with ether and washed once with dilute aqueous hydrochloric acid, three times with water, and once with brine. The organic phase is dried over magnesium sulfate and filtered. Argon is bubbled through the organic solution to remove residual hydrogen sulfide. The organic phase is concentrated in vacuo and the solid residue is crystallized from ether/hexane yielding 1.1 g (82%) of white crystals of 2-[3,5-bis((1,1-dimethylethyl)-4-hydroxyphenoxy]-ethanethioamide; mp 163.0°-164.0° C.

Workup

  1. washwashed once with dilute aqueous hydrochloric acid, three times with water
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. customArgon is bubbled through the organic solution
  5. customto remove residual hydrogen sulfide
  6. concentrationThe organic phase is concentrated in vacuo
  7. customthe solid residue is crystallized from ether/hexane yielding 1.1 g (82%) of white crystals of 2-[3,5-bis((1,1-dimethylethyl)-4-hydroxyphenoxy]-ethanethioamide

Sources & evidence

ORD record
ord-ad07c31d8d2e4fda892917f6815e1e09
Source dataset
uspto-grants-1992_04
Patent number
US05102897

Reaction notes

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