Tert-Butylamine → HCID 57962279, compound

HRID 541743Notes

Reaction equation

HRID 541743 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:11]([OH:14])(=[O:13])=O)[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[C:21]([NH2:25])([CH3:24])([CH3:23])[CH3:22].C(N(CC)C(C)C)(C)C>C1(C)C=CC=CC=1.Cl>[Br:1][C:2]1[CH:3]=[C:4]([S:11]([NH:25][C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:13])=[O:14])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 24819Phosphorus pentachlorideHCID 81531DiisopropylethylamineHCID 57961626HCID 57961626, compound

Product 1

HCID 57962279HCID 57962279, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-bromo-5-nitrobenzenesulfonic acid (1.86 g, 6.59 mmol) in toluene (37 mL) and phosphorus pentachloride (2.75 g, 13.2 mmol) were heated at 100° C. overnight. The reaction mixture was cooled to 0° C. and treated with tert-butylamine (1.03 mL, 9.89 mmol) and N,N-diisopropylethylamine (5.74 mL, 33.0 mmol). After stirring at 25° C. for 30 min, the reaction mixture was diluted with 1 N HCl and extracted with ethyl acetate three times. The combined organic layers were dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (2.2 g, 98%). 1H NMR (400 MHz, (400 MHz, DMSO-d6): δ 8.62 (m, 1H), 8.56 (m, 1H), 8.37 (m, 1H), 8.03 (s, 1H), 1.32 (s, 9H).

Workup

  1. extractionextracted with ethyl acetate three times
  2. dry with materialThe combined organic layers were dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-02c47eea0bf9411fbee6c0eef285b877
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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