Benzaldehyde → HCID 59717847, compound

HRID 601605Notes

Reaction equation

HRID 601605 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:22]=[CH:21][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]=[N+]=[N-])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1.[CH:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[BH4-].[Na+]>CO>[CH2:23]([NH:1][CH2:2][CH2:3][C:4]1[CH:22]=[CH:21][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH2:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 4311764Sodium borohydrideHCID 58835358HCID 58835358, compound

Product 1

HCID 59717847HCID 59717847, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Take up the mixture of 4-[4-(2-aminoethyl)phenoxy]benzenesulfonyl azide (0.210 g, 0.661 mmol) in methanol (9.9 mL). Add benzaldehyde (0.20 mL, 1.98 mmol) and 3 Å molecular sieves. Stir at room temperature overnight. Add NaBH4 (0.075 g, 1.98 mmol) and stir for 1.5 hours. Filter the reaction mixture and purify by flash 40 chromatography, eluting with 3% (2.0 M NH3 in methanol), 30% hexanes and 67% ethyl acetate to give the title compound (0.0696 g, 25.8%): TOF MS ES+383.1 (M+H)+, HRMS calcd for C21H23N2O3S 383.1429 (M+H)+. found 383.1436, time 0.33 min; TLC [silica gel 60 F254, 10% (2.0 M NH3 in methanol) in dichloromethane] Rf=0.31.

Workup

  1. filtrationFilter the reaction mixture
  2. custompurify by flash 40 chromatography
  3. washeluting with 3% (2.0 M NH3 in methanol), 30% hexanes and 67% ethyl acetate

Sources & evidence

ORD record
ord-cac1a7e7fb8c47bdb7a9589f01311281
Source dataset
uspto-grants-2011_03
Patent number
US07902372B2

Reaction notes

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