Hydrochloric Acid → 2,6-Dimethyl-4-[2-(2-methylphenyl)acetamido]benzenethiol

HRID 326789Notes

Reaction equation

HRID 326789 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([NH:10][C:11](=[O:20])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[CH:7]=[C:6]([CH3:21])[C:5]=1[S:22]C#N.O.Cl>C(O)C.C(COC)OC>[CH3:3][C:4]1[CH:9]=[C:8]([NH:10][C:11](=[O:20])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[CH:7]=[C:6]([CH3:21])[C:5]=1[SH:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 150159532,6-Dimethyl-4-[2-(2-methylphenyl)acetamido]phenyl thiocyanate

Product 1

HCID 150159512,6-Dimethyl-4-[2-(2-methylphenyl)acetamido]benzenethiol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Sodium borohydride (2.5 g, 66 mM) was added in portions to an ice-water cooled suspension of 2,6-dimethyl-4-[2-(2-methylphenyl)acetamido]phenyl thiocyanate (B) (5.0 g, 16 mM) in ethanol (100 mL) and dimethoxyethane (100 mL). After 2 hours, water (200 mL) was added to the clear yellow solution. The mixture was acidified to pH4 with 2M HCl and extracted with ethyl acetate. The combined extracts were washed with water, then with saturated sodium chloride solution, and dried (MgSO4). The solvent was removed by evaporation to yield 2,6-dimethyl-4-[2-(2-methylphenyl)acetamido]benzenethiol as a cream coloured solid (4.89 g) which was used without characterisation.

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with water
  4. dry with materialwith saturated sodium chloride solution, and dried (MgSO4)
  5. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-7738f63f33804c9ba3208794fc259aa5
Source dataset
uspto-grants-1993_12
Patent number
US05270342

Reaction notes

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