HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

2-Bromophenyl isocyanate → N-[3-(N''-Benzylaminosulfonyl)-4-chloro-2-hydroxyphenyl]-N'(2-bromophenyl) urea

HRID 2301499
Notes
Print preview

Reaction equation

HRID 2301499 reaction equation
[CH2:1]([NH:8][S:9]([C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[C:14]([NH2:19])[C:13]=1[OH:20])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]=[C:29]=[O:30]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([NH:8][S:9]([C:12]1[C:13]([OH:20])=[C:14]([NH:19][C:29]([NH:28][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[Br:21])=[O:30])[CH:15]=[CH:16][C:17]=1[Cl:18])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 1370972-Bromophenyl isocyanateHCID 18373453N-Benzyl-3-amino-6-chloro-2-hydroxybenzenesulfonamide

Product 1

HCID 11627629N-[3-(N''-Benzylaminosulfonyl)-4-chloro-2-hydroxyphenyl]-N'(2-bromophenyl) ureaYield 61%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl Acetate
Solvent

Procedure

A solution of N-benzyl-3-amino-6-chloro-2-hydroxybenzenesulfonamide (80 mg, 0.26 mmol) and 2-bromophenylisocyanate (47 μL, 0.38 mmol) in 2 mL of N,N-dimethylformamide was stirred at room temperature for 20 hours. The mixture was diluted with ethyl acetate and washed with water to give the crude material. Purification by column chromatography on silica gel, eluting with ethyl acetate/hexane (30/70 to 70/30, v/v), gave the desired product (80 mg, 61%). EI-MS (m/z) 508.1, 510.2, 512.2 (M−).

Workup

  1. washwashed with water
  2. customto give the crude material
  3. customPurification by column chromatography on silica gel
  4. washeluting with ethyl acetate/hexane (30/70 to 70/30, v/v)

Sources & evidence

ORD record
ord-4fb5ca65859f47ce82044d0aca034899
Source dataset
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06500863B1

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes