p-Toluenesulfonic acid → HCID 18403976, compound

HRID 1017624Notes

Reaction equation

HRID 1017624 reaction equation
C([O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)[CH:7]=1)(C)(C)C.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32]([OH:35])(=[O:34])=[O:33])=[CH:28][CH:27]=1>C1COCC1>[C:26]1([CH3:36])[CH:27]=[CH:28][C:29]([S:32]([O-:35])(=[O:33])=[O:34])=[CH:30][CH:31]=1.[OH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH+:9]=[C:8]([C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 18403981HCID 18403981, compound

Product 1

HCID 18403976HCID 18403976, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of crude compound 4 (6.5 g, 20 mmol) and p-toluenesulfonic acid (6.0 g, 30 mmol) in THF (150 mL) was heated under reflux for 4 h and then cooled to 0° C., the precipitate of 6 was filtered off and crystallized from methanol: yield 8.0 g (93%); mp 223-225° C.; 1H NMR (DMSO-d6) δ2.28 (s, 3), 7.10 (d, J=8 Hz, 2 H), 7.28 (s, 1 H), 7.50 (d, J=8 Hz, 2 H), 7.71 (m, 3 H), 8.0-8.215 (m, 6 H), 8.33 (d, J=8 Hz, 1 H), 8.61 (s, 1 H). Anal. Calcd for C26H21NO4S: C, 70.40; H, 4.77; N, 3.16. Found: C, 70.38; H, 4.73; N, 3.11.

Workup

  1. temperatureunder reflux for 4 h
  2. filtrationthe precipitate of 6 was filtered off
  3. customcrystallized from methanol

Sources & evidence

ORD record
ord-eadcfd0cc08d44e88f7d109196f115a5
Source dataset
uspto-grants-2002_11
Patent number
US06479504B1

Reaction notes

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