3-Bromoaniline → phenyl N-3-bromophenyl-N'-(methylsulfonyl)carbamimidate

HRID 1892138Notes

Reaction equation

HRID 1892138 reaction equation
[CH3:1][S:2]([N:5]=[C:6]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)OC1C=CC=CC=1)(=[O:4])=[O:3].[Br:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=1)[NH2:25]>C(#N)C>[Br:21][C:22]1[CH:23]=[C:24]([NH:25][C:6](=[N:5][S:2]([CH3:1])(=[O:3])=[O:4])[O:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 115623-BromoanilineHCID 13738851N-(Diphenoxymethylene)-methanesulfonamide

Product 1

HCID 68725987phenyl N-3-bromophenyl-N'-(methylsulfonyl)carbamimidateYield 52.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

Diphenyl methylsulfonylcarbonimidate from step A (0.75 g, 2.59 mmol) and 3-bromoaniline (0.28 ml, 2.59 mmol) were dissolved in acetonitrile (5 ml) and heated to 70° C. for 12 hours. The reaction was cooled to room temperature and concentrated under vacuum. Purification by flash chromatography (30% EtOAc/hexanes) afforded phenyl N-3-bromophenyl-N′-(methylsulfonyl)carbamimidate (0.50 g, 1.35 mmol, 52%).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated under vacuum
  3. customPurification by flash chromatography (30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d2f735eada964117b80eafd68b4076bc
Source dataset
uspto-grants-2013_08
Patent number
US08507672B2

Reaction notes

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