Triethylamine → HCID 18377848, compound

HRID 2298720Notes

Reaction equation

HRID 2298720 reaction equation
[N:1]1[N:2]([C:10]2[CH:11]=[C:12]([S:21](Cl)(=[O:23])=[O:22])[CH:13]=[C:14]([CH:17]([CH2:19][CH3:20])[CH3:18])[C:15]=2[OH:16])[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.Br.[Br:26][CH2:27][CH2:28][NH2:29].C(N(CC)CC)C>C(#N)C>[N:1]1[N:2]([C:10]2[CH:11]=[C:12]([S:21]([NH:29][CH2:28][CH2:27][Br:26])(=[O:23])=[O:22])[CH:13]=[C:14]([CH:17]([CH2:19][CH3:20])[CH3:18])[C:15]=2[OH:16])[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27742172-Bromoethylamine hydrobromideHCID 18377851HCID 18377851, compound

Product 1

HCID 18377848HCID 18377848, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a stirred suspension of 3-benzotriazol-2-yl-5-sec-butyl-4-hydroxybenzenesulfonyl chloride (14.19 g, 0.0388 mol) and 2-bromoethylamine hydrobromide (8.44 g, 0.0412 mol) in acetonitrile (100 g) at 0-5° C. under nitrogen was added dropwise a solution of triethylamine (8.05 g, 0.0796 mol) in acetonitrile (60 g). When the addition was complete, the reaction mixture was stirred at room temperature for 20 hours. The reaction mixture was suction filtered and the filter cake was washed with acetonitrile (20 g). The filtrate was spin-evaporated and the residue was suspended in water (130 g). The suspension was suction filtered and the filter cake was dried to give 10 g of 3-benzotriazol-2-yl-N-(2-bromoethyl)-5-sec-butyl-4-hydroxy-benzenesulfonamide as a white powder.

Workup

  1. additionWhen the addition
  2. filtrationfiltered
  3. washthe filter cake was washed with acetonitrile (20 g)
  4. customThe filtrate was spin-evaporated
  5. filtrationsuction filtered
  6. customthe filter cake was dried

Sources & evidence

ORD record
ord-7a2cdba6f8e241ada8ba4a667de5dcd8
Source dataset
uspto-grants-2002_12
Patent number
US06495125B2

Reaction notes

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