p-Toluenesulfonic acid → HCID 178457981, compound

HRID 1424194Notes

Reaction equation

HRID 1424194 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[NH:9][C:10](=O)[C:11]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:13])[CH3:12].CC1C=CC(S(O)(=O)=O)=CC=1>CO>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:10]([C:11]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([CH3:13])[CH3:12])=[N:9][C:3]=2[CH:4]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86699107HCID 86699107, compound

Product 1

HCID 178457981HCID 178457981, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of benzyl {2-[(2-amino-5-bromophenyl)amino]-1,1-dimethyl-2-oxoethyl}carbamate (Preparation 28, 80 g, 0.2 mol) and p-TsOH (34 g, 0.2 mol) in anhydrous MeOH (1 L) was heated to reflux for 48 hours. The reaction was cooled, concentrated in vacuo and partitioned between DCM (1 L) and water (500 mL). The organic layer was collected, washed with water (200 mL), brine (200 mL), dried over Na2SO4 and concentrated to low volume to enable the precipitation of a yellow solid. The solid was collected and dried to afford the title compound (18 g, 23%).

Workup

  1. temperatureto reflux for 48 hours
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated in vacuo
  4. custompartitioned between DCM (1 L) and water (500 mL)
  5. customThe organic layer was collected
  6. washwashed with water (200 mL), brine (200 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated to low volume
  9. customthe precipitation of a yellow solid
  10. customThe solid was collected
  11. customdried

Sources & evidence

ORD record
ord-7a42d2ccc5bf4a98b40e5ebada9b5b48
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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