Sodium Thiosulfate → N-(2,3-Dimethyl-1-oxobutan-2-yl)-3-methoxy-2-methylbenzamide

HRID 1091237Notes

Reaction equation

HRID 1091237 reaction equation
[OH:1][CH2:2][C:3]([NH:8][C:9](=[O:19])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[C:11]=1[CH3:18])([CH3:7])[CH:4]([CH3:6])[CH3:5].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[CH:2]([C:3]([NH:8][C:9](=[O:19])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[C:11]=1[CH3:18])([CH3:7])[CH:4]([CH3:5])[CH3:6])=[O:1]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 59713391HCID 59713391, compound

Product 1

HCID 59713395N-(2,3-Dimethyl-1-oxobutan-2-yl)-3-methoxy-2-methylbenzamideYield 101.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-(1-hydroxymethyl-1,2-dimethyl-propyl)-3-methoxy-2-methyl-benzamide (X, R1=2-Me-3-MeO-Ph, R2=i-Pr, R3=Me, 285 mg, 1.1 mmol) in CH2Cl2 (10 mL) at room temperature was added Dess-Martin periodinane solution (15% by weight, 2.4 mL, ca. 1.1 mmol). The mixture was stirred at room temperature for 4 h and poured into saturated aqueous NaHCO3 (50 mL). Solid Na2S2O3 (2.13 g, 8.6 mmol) was added and the mixture was stirred for 0.5 h. The mixture was extracted with ether (150 mL). The ether extract was washed with saturated aqueous NaHCO3 (50 mL), dried and evaporated under reduced pressure to afford N-(1-formyl-1,2-dimethyl-propyl)-3-methoxy-2-methyl-benzamide (293 mg) as an oil. 1H NMR (CDCl3) δ (ppm): 0.98 (d, J=6.6 Hz, 3H), 1.04 (d, J=6.6 Hz, 3H), 1.51 (s, 3H), 2.27 (s, 3H), 2.29 (m, 1H), 3.84 (s, 3H), 6.30 (br s, 1H), 6.91 (m, 1H), 6.96 (m, 1H), 7.18 (m, 1H), 9.60 (s, 1H).

Workup

  1. stirringthe mixture was stirred for 0.5 h
  2. extractionThe mixture was extracted with ether (150 mL)
  3. extractionThe ether extract
  4. washwas washed with saturated aqueous NaHCO3 (50 mL)
  5. customdried
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-3ae3317de4f3437a8d50821e23ccf160
Source dataset
uspto-grants-2012_03
Patent number
US08129355B2

Reaction notes

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