Water → HCID 296613, compound

HRID 2077697Notes

Reaction equation

HRID 2077697 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][C:8]=1[N+:17]([O-:19])=[O:18].O>ClCCl>[C:1]([NH:5][S:13]([C:10]1[CH:11]=[CH:12][C:7]([Cl:6])=[C:8]([N+:17]([O-:19])=[O:18])[CH:9]=1)(=[O:14])=[O:15])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6385Tert-ButylamineHCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-

Product 1

HCID 296613HCID 296613, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of tert-butylamine (5.1 g, 70 mmol) in dichloromethane (200 mL) was added dropwise a solution of 4-chloro-3-nitrobenzenesulfonyl chloride (17.9 g, 70 mmol) in dichloromethane (100 mL) at room temperature over a period of 30 min, and then the reaction mixture was stirred for 2 h. The reaction mixture was poured into water (100 mL), the organic phase was separated, and the aqueous phase was extracted with ethyl acetate (100 mL). The combined organic extracts were washed with water (50 mL) and brine (20 mL), dried (Na2SO4), and concentrated to give 21.3 g (quant.) of the title compound as yellow solids: 1H-NMR (CDCl3) δ 8.38 (1H, d, J=2.0 Hz), 8.02 (1H, dd, J=2.0, 8.6 Hz), 7.70 (1H, d, J=8.6 Hz), 4.95 (1H, br.s), 1.28 (9H, s).

Workup

  1. customthe organic phase was separated
  2. extractionthe aqueous phase was extracted with ethyl acetate (100 mL)
  3. washThe combined organic extracts were washed with water (50 mL) and brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-45d5d0f7cb0446ada3be47eea1f708d7
Source dataset
uspto-grants-2011_04
Patent number
US07928119B2

Reaction notes

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