Water → 5-(aminomethyl)-2-chloro-N-cyclopropylbenzenesulfonamide

HRID 1845149Notes

Reaction equation

HRID 1845149 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([Cl:18])=[C:9]([S:11]([NH:14][CH:15]2[CH2:17][CH2:16]2)(=[O:13])=[O:12])[CH:10]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[NH2:1][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([Cl:18])=[C:9]([S:11]([NH:14][CH:15]2[CH2:17][CH2:16]2)(=[O:13])=[O:12])[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 866521075-(azidomethyl)-2-chloro-N-cyclopropylbenzenesulfonamide

Product 1

HCID 657697715-(aminomethyl)-2-chloro-N-cyclopropylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A round bottom flask was charged with 5-(azidomethyl)-2-chloro-N-cyclopropylbenzenesulfonamide (1.40 g, 4.87 mmol), THF (40 mL), triphenylphosphine (1.6 g, 6.43 mmol) and water (0.11 mL, 6.43 mmol) at 0° C. and the reaction was stirred at room temperature over night. The solvents were removed and the residue was dissolved in MTBE and 20% HCl in dioxane was added dropwise at 0° C. The resulting salt was collected and washed with EtOAc. The salt was then neutralized with 6N NaOH and extracted with CH2Cl2. The combined organic phases were concentrated under reduced pressure to get the title product as a very thick oil. 1H NMR (400 MHz, DMSO-d6): 8.00 (s, 1H), 7.58 (s, 2H), 3.78 (s, 2H), 2.18 (m, 1H), 0.50-0.35 (m, 4H).

Workup

  1. customThe solvents were removed
  2. dissolutionthe residue was dissolved in MTBE
  3. addition20% HCl in dioxane was added dropwise at 0° C
  4. customThe resulting salt was collected
  5. washwashed with EtOAc
  6. extractionextracted with CH2Cl2
  7. concentrationThe combined organic phases were concentrated under reduced pressure

Sources & evidence

ORD record
ord-0dd6ae224f0a451cae45a6181f20af8e
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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