Dimethyl Sulfoxide → 4-(cyanomethyl)-3-methoxy-N-(2-oxocyclohexyl)benzamide

HRID 7797

Reaction equation

HRID 7797 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([CH2:13][C:14]1[CH:29]=[CH:28][C:17]([C:18]([NH:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]2[OH:27])=[O:19])=[CH:16][C:15]=1[O:30][CH3:31])#[N:12]>ClCCl>[C:11]([CH2:13][C:14]1[CH:29]=[CH:28][C:17]([C:18]([NH:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][C:22]2=[O:27])=[O:19])=[CH:16][C:15]=1[O:30][CH3:31])#[N:12]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 695845884-(cyanomethyl)-N-[(2R)-2-hydroxycyclohexyl]-3-methoxybenzamide

Product 1

HCID 219909934-(cyanomethyl)-3-methoxy-N-(2-oxocyclohexyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
22 °C

Procedure

To a solution of oxalyl chloride (0.2 mL, 2.2 mmol) in anhydrous dichloromethane (2 mL) at −78° C. was added DMSO (0.32 mL, 4.5 mmol) under Argon. The solution was maintained for 10 min where upon a solution of 4-(cyanomethyl)-N-[(2R)-2-hydroxycyclohexyl]-3-methoxybenzamide (430 mg, 1.5 mmol) in anhydrous dichloromethane (13 mL) was added dropwide. The reaction was stirred at −78° C. for 30 min, whereupon TEA (1 mL, 7.5 mmol) was added. The reaction was warmed to 22° C. for 2 h. Then, 50 mL dichloromethane was added to the mixture, washed with sat NaHCO3 (3×15 mL) and sat. brine (3×15 mL), dried (MgSO4), and concentrated to afford a yellow solid of 4-(cyanomethyl)-3-methoxy-N-(2-oxocyclohexyl)benzamide. MS (ESI) 287 (M+H)+.

Workup

  1. additionwas added dropwide
  2. additionwas added
  3. washwashed with sat NaHCO3 (3×15 mL) and sat. brine (3×15 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ab1f6b7ec2ca44eb9d2a0d552c7197c3
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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