Triethylamine → N-[2-Chloro-4-{4-(N,N-dimesylamino)phenylsulphanyl}phenyl]-2-acetoxy-2-methylpropanamide

HRID 2301058Notes

Reaction equation

HRID 2301058 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:16][C:17](=[O:25])[C:18]([O:21][C:22](=[O:24])[CH3:23])([CH3:20])[CH3:19].C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([S:8][C:9]2[CH:10]=[CH:11][C:12]([N:15]([S:34]([CH3:33])(=[O:36])=[O:35])[S:34]([CH3:33])(=[O:36])=[O:35])=[CH:13][CH:14]=2)[CH:5]=[CH:4][C:3]=1[NH:16][C:17](=[O:25])[C:18]([O:21][C:22](=[O:24])[CH3:23])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22287369N-[2-Chloro-4-(4-aminophenylsulphanyl)phenyl]-2-acetoxy-2-methylpropanamide

Product 1

HCID 22287442N-[2-Chloro-4-{4-(N,N-dimesylamino)phenylsulphanyl}phenyl]-2-acetoxy-2-methylpropanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

N-[2-Chloro-4-(4-aminophenylsulphanyl)phenyl]-2-acetoxy-2-methylpropanamide (Method 22) (0.50 g) was dissolved in DCM (10 ml) and cooled to 0-5° C. in an ice bath. Triethylamine (0.55 ml) was added followed by dropwise addition of methylsulphonyl chloride (0.11 ml) and the mixture was allowed to warm to ambient temperature over 2 hours. The solution was concentrated then the solid was dissolved in DCM (5 ml) and water (5 ml) was added. The solution was loaded onto a Varian Chem Elut column and after 3 minutes was washed through with DCM (20 ml). The DCM layer was then concentrated and the solid washed with ether and filtered to give the title compound (0.58 g) as a solid. NMR (CDCl3): 1.7 (s, 6H), 2.2 (s, 3H), 3.4 (s, 6H), 7.2 (s, 4H), 7.4 (d, 1H), 7.5 (d, 1H), 8.4 (d, 1H), 8.5 (d, 1H); MS (ESP−): 533; EA: found: C, 44.4; H, 4.5; N, 5.1%; C20H23ClN2O7S3 requires C, 44.9; H, 4.3; N, 5.2%.

Workup

  1. temperatureto warm to ambient temperature over 2 hours
  2. concentrationThe solution was concentrated
  3. dissolutionthe solid was dissolved in DCM (5 ml)
  4. additionwater (5 ml) was added
  5. washwas washed through with DCM (20 ml)
  6. concentrationThe DCM layer was then concentrated
  7. washthe solid washed with ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-64ba7fd20a1041dfb89ad67dfd693e1b
Source dataset
uspto-grants-2002_12
Patent number
US06498275B1

Reaction notes

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