Triethylamine → HCID 11287490, compound

HRID 1735019Notes

Reaction equation

HRID 1735019 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].Cl[CH2:13][CH2:14][CH2:15][C:16](Cl)=O.C(N(CC)CC)C>O1CCCC1.[OH-].[Na+]>[O:10]=[S:8]1(=[O:9])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]2[CH2:13][CH2:14][CH2:15][C:16]2=[N:11]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 728942-AminobenzenesulfonamideHCID 783704-Chlorobutyryl chloride

Product 1

HCID 11287490HCID 11287490, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

5.8 mmol of 2-aminobenzenesulfonamide are dissolved in tetrahydrofuran (THF) at room temperature. This solution is cooled on an ice bath, and 6 mmol of 4-chlorobutanoyl chloride and 6 mmol of triethylamine are successively added. The mixture is stirred for 16 hours at room temperature, filtered and evaporated. The yellow solid obtained is taken up in 40 ml of 1N sodium hydroxide and stirred at room temperature. After complete dissolution, a white precipitate appears; it is filtered off and gives the expected product after crystallization from an ethanol/water (4/1) mixture.

Workup

  1. temperatureThis solution is cooled on an ice bath
  2. filtrationfiltered
  3. customevaporated
  4. customThe yellow solid obtained
  5. stirringstirred at room temperature
  6. dissolutionAfter complete dissolution
  7. filtrationit is filtered off

Sources & evidence

ORD record
ord-77f896765c3a4ea9a45ca0634ed37901
Source dataset
uspto-grants-1996_07
Patent number
US05536719

Reaction notes

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