Water → HCID 86729561, compound

HRID 2280574Notes

Reaction equation

HRID 2280574 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[Cl:18][C:19]1[C:20]([C:29](Cl)=[O:30])=[N:21][C:22]2[C:27]([N:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2.O>ClCCl>[Cl:18][C:19]1[C:20]([C:29]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([S:8](=[O:9])(=[O:10])[NH2:11])[CH:3]=2)=[O:30])=[N:21][C:22]2[C:27]([N:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7377Benzenesulfonamide, 3-amino-HCID 19995701HCID 19995701, compound

Product 1

HCID 86729561HCID 86729561, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-aminobenzenesulfonamide (4.5 g, 26.43 mmol) and pyridine (12.83 mL, 158.6 mmol) in dichloromethane (48 mL) at 0° C. was added 3-chloroquinoxaline-2-carbonyl chloride (6.0 g, 26.43 mmol) in dichloromethane (60 mL) and the mixture was stirred and allowed to warm up to room temperature overnight. To the reaction slurry, water (60 mL) was added. The solid was isolated by filtration, washed with water (3×50 mL), hexane (50 mL) and a small amount of dichloromethane. The solid was dried under vacuum to yield 3-chloro-N-(3-sulfamoylphenyl)quinoxaline-2-carboxamide (7.1 g, 74%) as a salmon colored solid. ESI-MS m/z calc. 362.02, found 363.3 (M+1)+; Retention time: 1.43 minutes (3 minutes run). 1H NMR (400 MHz, DMSO-d6) δ 11.30 (s, 1H), 8.40-8.33 (m, 1H), 8.31-8.24 (m, 1H), 8.24-8.14 (m, 1H), 8.12-7.98 (m, 2H), 7.90-7.81 (m, 1H), 7.69-7.58 (m, 2H), 7.47 (s, 2H) ppm.

Workup

  1. customThe solid was isolated by filtration
  2. washwashed with water (3×50 mL), hexane (50 mL)
  3. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-97574c47b6354251a3e9a940a8dc03dd
Source dataset
uspto-grants-2015_09
Patent number
US09139529B2

Reaction notes

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