4-Toluenesulfonyl chloride → HCID 10092233, compound

HRID 2090232Notes

Reaction equation

HRID 2090232 reaction equation
C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[C:12]([O:16][C:17](=[O:40])[NH:18][CH2:19][CH2:20][CH2:21][N:22]1[C:34]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N+:27]([O-])=[CH:26][C:25]=2[N:24]=[C:23]1[CH2:36][CH2:37][CH2:38][CH3:39])([CH3:15])([CH3:14])[CH3:13].[OH-].[NH4+:42]>C(Cl)Cl>[C:12]([O:16][C:17](=[O:40])[NH:18][CH2:19][CH2:20][CH2:21][N:22]1[C:34]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N:27]=[C:26]([NH2:42])[C:25]=2[N:24]=[C:23]1[CH2:36][CH2:37][CH2:38][CH3:39])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 22478983HCID 22478983, compound

Product 1

HCID 10092233HCID 10092233, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

p-Toluenesulphonyl chloride (0.43 g) was added portionwise to a vigourously stirred mixture of the product from step (v) (0.9 g) in DCM (25 mL) and ammonium hydroxide solution (35%, 2.5 mL) at 0° C. The mixture was allowed to warm to rt over 2 h then partitioned between water/DCM, washed with saturated sodium bicarbonate solution, dried, filtered and the solvent evaporated. The solid product was triturated with diethylether to give the subtitle compound (0.6 g).

Workup

  1. customthen partitioned between water/DCM
  2. washwashed with saturated sodium bicarbonate solution
  3. customdried
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customThe solid product was triturated with diethylether

Sources & evidence

ORD record
ord-f5a5fd53a7c149b082bedf4ed81f295f
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

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