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

HRID 1062402Notes

Reaction equation

HRID 1062402 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 m) 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-50e56618b206476ab29002817ca3d230
Source dataset
uspto-grants-2005_11
Patent number
US06960688B2

Reaction notes

Loading…