4-Methylbenzenethiol → HCID 68278129, compound

HRID 931491Notes

Reaction equation

HRID 931491 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8].[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([SH:26])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O>[CH3:8][C:7]1[O:6][C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)=[N:4][C:3]=1[CH2:2][S:26][C:23]1[CH:24]=[CH:25][C:20]([CH3:19])=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 78114-MethylbenzenethiolHCID 10796Cesium carbonateHCID 23076573Methyl 4-(4-(chloromethyl)-5-methyloxazol-2-yl)benzoate

Product 1

HCID 68278129HCID 68278129, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 4-(4-(chloromethyl)-5-methyloxazol-2-yl)benzoate (6 g, 22.64 mmol, 1.00 equiv), 4-methylbenzenethiol (4.2 g, 33.87 mmol) and cesium carbonate (8.8 g, 26.99 mmol, 1.19 equiv) in N,N-dimethylformamide (120 mL) was stirred under nitrogen overnight at 50° C. The reaction mixture was diluted with 100 mL of water and extracted with 3×150 mL of ethyl acetate. The combined organic layers was washed with 3×50 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was triturated with 2×50 mL of hexane. The solid was collected by filtration and dried in vacuum to yield 6.2 g (78%) of methyl 4-(5-methyl-4-(p-tolylthiomethyl)oxazol-2-yl)benzoate as a yellow solid. LC-MS: (ES, m/z): 395 [M+CH3CN+H]+, 354 [M+H]+, 271, 203, 126, 120.

Workup

  1. extractionextracted with 3×150 mL of ethyl acetate
  2. washThe combined organic layers was washed with 3×50 mL of brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was triturated with 2×50 mL of hexane
  6. filtrationThe solid was collected by filtration
  7. customdried in vacuum

Sources & evidence

ORD record
ord-4275f0aa487f43bfaf02b6b3762943ba
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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