Dimethylamine → HCID 57722500, compound

HRID 1986619Notes

Reaction equation

HRID 1986619 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:15]=[CH:14][C:13]2[CH2:12][CH2:11][C:10](=[O:16])[CH2:9][C:8]=2[CH:7]=1)(=[O:5])=[O:4].N(C)[CH3:18]>C(Cl)Cl>[CH3:1][N:2]([CH3:18])[S:3]([C:6]1[CH:15]=[CH:14][C:13]2[CH2:12][CH2:11][C:10](=[O:16])[CH2:9][C:8]=2[CH:7]=1)(=[O:4])=[O:5]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 57722504HCID 57722504, compound

Product 1

HCID 57722500HCID 57722500, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 7-oxo-5,6,7,8-tetrahydro-naphthalene-2-sulfonyl chloride (see Preparative Example 3, 1.0 g, 4.1 mmol) in CH2Cl2 (10 mL) at 15° C. (using a water bath) was added Me2NH (2M in THF, 8 mL, 16 mmol, 4 eq) dropwise. After stirring at room temperature for 30 minutes, the mixture was diluted with CH2Cl2 (30 mL), washed with H2O (20 mL), dried (Na2SO4), and concentrated. The residue was chromatographed on silica using 20% EtOAc/hexanes to give 0.46 g (45%) of 7-oxo-5,6,7,8-tetrahydro-naphthalene-2-sulfonic acid dimethylamide as a yellow oil. 1H NMR (300 MHz, CDCl3): δ 7.61 (d, 1H, J=8.1 Hz), 7.53 (s, 1H), 7.41 (d, 1H, J=8.1 Hz), 3.65 (s, 2H), 3.14 (t, 2H, J=6.6 Hz), 2.71 (s, 6H), 2.58 (t, 2H, J=6.6 Hz).

Workup

  1. washwashed with H2O (20 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica using 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-c9007ce84fc647459e756b2f4c3cf16c
Source dataset
uspto-grants-2009_06
Patent number
US07550467B2

Reaction notes

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