Dichloromethane → Benzyl 3-cyano-2-methyl-6-[(phenylsulfonyl)amino]benzoate

HRID 1725889Notes

Reaction equation

HRID 1725889 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[C:6]([CH3:18])[C:5]([C:19]#[N:20])=[CH:4][CH:3]=1.ClCCl.[C:24]1([S:30](Cl)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>N1C=CC=CC=1>[C:19]([C:5]1[C:6]([CH3:18])=[C:7]([C:2]([NH:1][S:30]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:32])=[O:31])=[CH:3][CH:4]=1)[C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9])#[N:20]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7369Benzenesulfonyl chlorideHCID 68863942Benzyl 6-amino-3-cyano-2-methylbenzoate

Product 1

HCID 68865363Benzyl 3-cyano-2-methyl-6-[(phenylsulfonyl)amino]benzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of Example 108B (576 mg, 2.2 mmol), anhydrous dichloromethane (22 mL), pyridine (0.4 mL) and benzenesulfonyl chloride (0.33 mL) was stirred 18 hours under nitrogen atmosphere. The mixture was concentrated, dissolved in ethyl acetate (100 mL), washed with 0.5M HCl (3×50 mL) and brine, dried (Na2SO4), filtered, concentrated, and purified on silica gel (20 g) with 50% dichloromethane in hexanes to provide the desired product. MS (ESI(+)) m/e 407 (M+H)+, 424 (M+NH4)+, 429 (M+Na)+; (ESI(−)) m/e 405 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 10.59 (br s, 1H), 7.77 (m, 3H), 7.64 (m, 1H), 7.56-7.37 (m, 7H), 7.24 (d, 1H), 5.31 (s, 2H), 2.32 (s, 3H).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in ethyl acetate (100 mL)
  3. washwashed with 0.5M HCl (3×50 mL) and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified on silica gel (20 g) with 50% dichloromethane in hexanes

Sources & evidence

ORD record
ord-e5e456656c9c46729f87b92ebd30ab55
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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