4-Toluenesulfonyl chloride → HCID 12041758, compound

HRID 1263636Notes

Reaction equation

HRID 1263636 reaction equation
[OH:1][CH2:2][CH:3]1[O:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]3[NH:15][C:14](=[O:16])[NH:13][C:10]3=2)[CH2:5][CH2:4]1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>N1C=CC=CC=1>[O:16]=[C:14]1[NH:13][C:10]2=[C:11]3[C:6](=[CH:7][CH:8]=[C:9]2[NH:15]1)[CH2:5][CH2:4][CH:3]([CH2:2][O:1][S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=1)(=[O:25])=[O:24])[O:12]3

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 12041757HCID 12041757, compound

Product 1

HCID 12041758HCID 12041758, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 8-hydroxymethyl-3,6,7,8-tetrahydro-1H-9-oxa-1,3-diaza-cyclopenta[a]naphthalen-2-one (331 mg, 1.5 mmol) and p-toluenesulfonyl chloride (572 mg, 3 mmol) in anhydrous pyridine (50 mL) was stirred for 12 hours followed by removal of the solvent in vacuo to a residue. The residue was dissolved in ethyl acetate (100 mL) and washed with water (3×30 mL). The organic layer was dried over anhydrous Na2SO4 and filtered. The solvent was removed in vacuo to a residue followed by chromatography (20% CH2Cl2-hexanes) to afford 466 mg (83%) of the title compound as a solid: mp 205° C.; 1H NMR (400 MHz, CDCl3): 1.87 (m, 1H), 2.02 (m, 1H), 2.48 (s, 3H), 2.81 (m, 2H), 4.22 (m, 2H), 4.31 (m, 1H), 6.56 (d, J=8.0 Hz, 1H), 6.70 (d, J=8.0 Hz, 1H), 7.38 (d, J=8.1 Hz, 2H), 7.58 (s, 1H), 7.83 (d, J=8.1 Hz, 1H), 8.18 (s, 1H); IR: 3280, 3000, 2950, 1700, 1510, 1350 cm−1; MS 375 [M+H]+.

Workup

  1. customfollowed by removal of the solvent in vacuo to a residue
  2. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  3. washwashed with water (3×30 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo to a residue

Sources & evidence

ORD record
ord-ec6f8ed2a105430091dd503d707f048d
Source dataset
uspto-grants-2003_04
Patent number
US06541502B1

Reaction notes

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