Sodium Carbonate → Methyl 4-(4-{[(4-tert-Butylphenyl)sulfonyl]methyl}-5-methyl-1,3-oxazol-2-yl)benzoate

HRID 931429Notes

Reaction equation

HRID 931429 reaction equation
[O-]S([O-])=O.[Na+].[Na+].C([O-])([O-])=O.[Na+].[Na+].[C:13]([C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14].Cl[CH2:28][C:29]1[N:30]=[C:31]([C:35]2[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][CH:36]=2)[O:32][C:33]=1[CH3:34]>O.CCO>[C:13]([C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH2:28][C:29]2[N:30]=[C:31]([C:35]3[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][CH:36]=3)[O:32][C:33]=2[CH3:34])(=[O:25])=[O:24])=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 24437Sodium SulfiteHCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 23076573Methyl 4-(4-(chloromethyl)-5-methyloxazol-2-yl)benzoate

Product 1

HCID 68278317Methyl 4-(4-{[(4-tert-Butylphenyl)sulfonyl]methyl}-5-methyl-1,3-oxazol-2-yl)benzoateYield 26.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent3×

Conditions

Temperature
100 °C

Procedure

A solution of Na2SO3 (126 mg, 1.0 mmol) and Na2CO3 (106 mg, 1.0 mmol) in water (2 mL) was added to a suspension of 4-tert-butylbenzenesulfonyl chloride (233 mg, 1.0 mmol) in water (5 mL) and the mixture was stirred at 100° C. for 2 h. A solution of chloride 2 (268 mg, 1.0 mmol) in EtOH (5 mL) was added and the mixture stirred at 100° C. for 16 h. The mixture was cooled and diluted with water (40 mL) and stirred for 15 min. The precipitate was filtered, washed with water (5 mL). The residue purified by column chromatography, eluting with a gradient (20-50%) of EtOAc/pet. ether, to give benzoate 22 (112 mg, 26%) as a white powder: mp (EtOAc) 190-192° C.; 1H NMR (CDCl3) δ 8.05 (ddd, J=8.6, 1.8, 1.5 Hz, 2H, H-2, H-6), 7.89 (ddd, J=8.6, 1.8, 1.5 Hz, 2H, H-3, H-5), 7.71 (ddd, J=8.6, 2.2, 1.8 Hz, 2H, H-2′, H-6′), 7.51 (ddd, J=8.6, 2.2, 1.8 Hz, 2H, H-3′, H-5′), 4.30 (s, 2H, CH2SO2), 3.94 (s, 3H, OCH3), 2.32 (s, 3H, CH3), 1.33 [s, 9H, C(CH3)3]; MS m/z 428.5 (MH+, 100%). Anal. calcd for C23H25NO5S: C, 64.62; H, 5.89; N, 3.28. Found: C, 64.70; H, 5.94; N, 3.25%.

Workup

  1. stirringthe mixture stirred at 100° C. for 16 h
  2. temperatureThe mixture was cooled
  3. stirringstirred for 15 min
  4. filtrationThe precipitate was filtered
  5. washwashed with water (5 mL)
  6. customThe residue purified by column chromatography
  7. washeluting with a gradient (20-50%) of EtOAc/pet. ether

Sources & evidence

ORD record
ord-bb13505d50a347c89092de3c8ac76ee7
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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