Toluene → HCID 69132655, compound

HRID 988219Notes

Reaction equation

HRID 988219 reaction equation
O[C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[C:9]2[NH:14][C:13](=[O:15])[C:12](=[CH:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[NH:11][C:10]2=[O:24])=[N:6][CH:7]=1.[C:25]1(C)[C:26]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:28]=[CH:29][CH:30]=1.[C:36]1(C)C=CC=CC=1>C(Cl)Cl>[C:29]1([CH3:36])[CH:30]=[CH:25][C:26]([S:31]([C:2]2[CH:3]=[CH:4][C:5]([CH:8]=[C:9]3[NH:14][C:13](=[O:15])[C:12](=[CH:16][CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[NH:11][C:10]3=[O:24])=[N:6][CH:7]=2)(=[O:32])=[O:33])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 8623o-Toluenesulfonyl chlorideHCID 69132345HCID 69132345, compound

Product 1

HCID 69132655HCID 69132655, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

A reaction mixture of compound B (0.05 g, 0.16 mmole; obtained from Example 14), toluenesulfonyl chloride (0.03 g, 0.16 mmole), and 50 mL of toluene was heated to 150° C. for 2 hr. Toluene was removed in vacuo to produce a residue. The residue was chromatographied using silica gel column with a developing solvent (CH2Cl2) to give 0.007 g (10%) of Compound 16.

Workup

  1. customToluene was removed in vacuo
  2. customto produce a residue

Sources & evidence

ORD record
ord-3970525b139b46ddb24dd3e74349e2cf
Source dataset
uspto-grants-2003_10
Patent number
US06635649B2

Reaction notes

Loading…