2-Nitrobenzenesulfonyl chloride → HCID 5461210, compound

HRID 1842457Notes

Reaction equation

HRID 1842457 reaction equation
[CH2:1]([NH2:4])[C:2]#[CH:3].C(N(CC)C(C)C)(C)C.[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23](Cl)(=[O:25])=[O:24])([O-:16])=[O:15]>C(Cl)Cl>[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23]([NH:4][CH2:1][C:2]#[CH:3])(=[O:25])=[O:24])([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 239041Propargylamine

Product 1

HCID 5461210HCID 5461210, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of propargylamine (2 mL, 29 mmol) and N,N-diisopropylethylamine (10 mL, 57.4 mmol) in methylene chloride (100 mL) was cooled to 0° C. 2-nitrobenzenesulfonyl chloride (6.46 g, 29.2 mmol) was added portionwise. Upon complete addition, the solution was allowed to warm to room temperature and was further stirred at room temperature overnight. The reaction solution was concentrated in vacuo and the residue obtained was directly purified on silica chromatography (20-50% EtOAc/hexane) to afford Intermediate 14 as white solid (5.90 g, 84%). LC-MS: (FA) ES+241; 1H NMR (400 MHz, CDCl3) δ 8.22-8.17 (m, 1H), 7.94-7.89 (m, 1H), 7.79-7.73 (m, 2H), 5.71 (s, 1H), 4.02 (dd, J=5.9, 2.4 Hz, 2H), 1.97 (t, J=2.5 Hz, 1H).

Workup

  1. additionUpon complete addition
  2. concentrationThe reaction solution was concentrated in vacuo
  3. customthe residue obtained
  4. customwas directly purified on silica chromatography (20-50% EtOAc/hexane)

Sources & evidence

ORD record
ord-75e12ee736a44540ac41e0ac976c3d8c
Source dataset
uspto-grants-2015_02
Patent number
US08946223B2

Reaction notes

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