4-Methylbenzenethiol → HCID 23362221, compound

HRID 1082118Notes

Reaction equation

HRID 1082118 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[H-].[Na+].[O:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[N:20]([CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH:32](Cl)[C:33]([O:35][CH3:36])=[O:34])=[CH:27][CH:26]=1)[CH3:21]>CN(C)C=O.O>[O:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[N:20]([CH2:22][CH2:23][O:24][C:25]1[CH:26]=[CH:27][C:28]([CH2:31][CH:32]([S:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[C:33]([O:35][CH3:36])=[O:34])=[CH:29][CH:30]=1)[CH3:21]

Participants

6

Reactant 3

HCID 78114-MethylbenzenethiolHCID 24758Sodium hydrideHCID 15186152HCID 15186152, compound

Product 1

HCID 23362221HCID 23362221, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

ρ-Thiocresol (0.43 g) was added slowly to an ice-cooled, stirred suspension of sodium hydride (60% dispersion in oil, 0.14 g) in dry N, N-dimethylformamide (23 mL,) under N2. The mixture was allowed to warm to room temperature over 30 minutes prior to the addition of a solution of methyl 3-[4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]phenyl]-2-chloropropanoate (1.31 g) in dry N,N-dimethylformamide (16 mL) and the mixture was then left stirring at room temperature for a further 12 hrs. The reaction mixture was diluted with water (375 mL) before extracting with ethyl acetate (3×100 mL). The combined ethyl acetate layers were washed with water (3×100 mL), dried (MgSO4) and evaporated. The residue was chromatographed on silica gel using 60% hexane in ethyl acetate as eluent to afford the title compound which solidified on standing, mp 88.6°-90.1° C.

Workup

  1. temperaturecooled
  2. waitthe mixture was then left
  3. stirringstirring at room temperature for a further 12 hrs
  4. extractionbefore extracting with ethyl acetate (3×100 mL)
  5. washThe combined ethyl acetate layers were washed with water (3×100 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was chromatographed on silica gel using 60% hexane in ethyl acetate as eluent

Sources & evidence

ORD record
ord-9141202cc5bc43d084f7bc91e3e011c9
Source dataset
uspto-grants-1996_12
Patent number
US05589492

Reaction notes

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