4-Chloro-3-nitrobenzenesulfonamide → HCID 67227854, compound

HRID 2273741Notes

Reaction equation

HRID 2273741 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][NH:8][C:7](=[O:11])[CH2:6]1.C(N(CC)CC)C.O1CCOCC1.Cl[C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH2:35])(=[O:34])=[O:33])=[CH:28][C:27]=1[N+:36]([O-:38])=[O:37]>CN(C)C(=O)C>[N+:36]([C:27]1[CH:28]=[C:29]([S:32]([NH2:35])(=[O:33])=[O:34])[CH:30]=[CH:31][C:26]=1[NH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][NH:8][C:7](=[O:11])[CH2:6]1)([O-:38])=[O:37]

Participants

6

Reactant 4

HCID 73244-Chloro-3-nitrobenzenesulfonamideHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 167839134-(3-Aminopropyl)piperazin-2-one

Product 1

HCID 67227854HCID 67227854, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

4-(3-Amino-propyl)-piperazin-2-one (3.45 g) and triethylamine (5.18 mL, 3.76 g) were added to 1,4-dioxane (100 mL) and N,N-dimethylacetamide (20 mL) and mixed until dissolved. 4-Chloro-3-nitrobenzenesulfonamide (4.00 g) was added, and the mixture was heated to 90° C. for 16 hours. The mixture was cooled and the solvent was removed under vacuum. The material purified by recrystallization from 20% methanol in dichloromethane with subsequent washing of the recrystallized solid with 10% methanol in dichloromethane followed by washing with 100% dichloromethane.

Workup

  1. additionmixed
  2. dissolutionuntil dissolved
  3. temperatureThe mixture was cooled
  4. customthe solvent was removed under vacuum
  5. customThe material purified by recrystallization from 20% methanol in dichloromethane
  6. washwith subsequent washing of the recrystallized solid with 10% methanol in dichloromethane
  7. washby washing with 100% dichloromethane

Sources & evidence

ORD record
ord-68cd7ae256a74723a4bdf27eb4821c3a
Source dataset
uspto-grants-2015_09
Patent number
US09125913B2

Reaction notes

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