4-Toluenesulfonyl chloride → HCID 57991620, compound

HRID 556105Notes

Reaction equation

HRID 556105 reaction equation
[CH2:1]([C:8]1[S:12][C:11]([NH2:13])=[N:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH2:27][CH3:28])CC)C.[C:29]1([CH3:39])[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>C1COCC1>[CH2:1]([C:8]1[S:12][C:11]([N:13]([S:35]([C:32]2[CH:33]=[CH:34][C:27]([CH3:28])=[CH:30][CH:31]=2)(=[O:37])=[O:36])[S:35]([C:32]2[CH:33]=[CH:34][C:29]([CH3:39])=[CH:30][CH:31]=2)(=[O:37])=[O:36])=[N:10][C:9]=1[C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 137372225-Benzyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine

Product 1

HCID 57991620HCID 57991620, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 100 ml eggplant-shaped flask were added 1.00 g (3.37 mmol) 5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine prepared in Example 1, 0.68 g (6.75 mmol) triethylamine and 25 ml THF, added dropwise 1.28 g (6.74 mmol) p-tolylsulfonyl chloride which was dissolved in 5 ml THF. The resulting mixture was stirred at room temperature for 24 hours, filtered, washed with THF, the mother liquid was concentrated under a reduced pressure to a give crude product, which was recrystallized with acetone to obtain a 1.04 g product as a off-white solid in a yield of 51.0%, mp: 182-183 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 2.45 (6H, s, 2×PhCH3), 3.84 (3H, s, OCH3), 4.26 (2H, s, CH2), 6.92 (2H, d, J=8.68 Hz, ArH), 7.18˜7.36 (9H, m, ArH), 7.46 (2H, d, J=8.68 Hz, ArH), 7.92 (4H, d, J=8.68 Hz, ArH); EI-MS m/e (%): 604.2 (M+, 19), 450.2 (44), 294.2 (78), 91.1 (100); HREI-MS Calcd. for C31H28N2O5S3: 604.1160. found: 604.1165. Anal. Calcd. for C31H28N2O5S3: C, 61.57; H, 4.67; N, 4.63. found: C, 61.71; H, 4.49; N, 4.82.

Workup

  1. filtrationfiltered
  2. washwashed with THF
  3. concentrationthe mother liquid was concentrated under a reduced pressure to
  4. customa give crude product, which
  5. customwas recrystallized with acetone

Sources & evidence

ORD record
ord-e0a5a52147074437aafc933b396e7ce9
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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