2-Tolyl isocyanate → HCID 21963303, compound

HRID 2211867Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[CH:20][C:19]=3[NH2:28])[CH2:12][CH2:11]2)=[N:2]1.[C:29]1([CH3:38])[C:30]([N:35]=[C:36]=[O:37])=[CH:31][CH:32]=[CH:33][CH:34]=1>C(Cl)Cl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[CH:20][C:19]=3[NH:28][C:36]([NH:35][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[CH3:38])=[O:37])[CH2:14][CH2:15]2)=[N:2]1

Participants

Conditions

Temperature: 40 °C

Procedure

2-[2-(4-1,2-Benzisothiazol-3-yl-piperazin-1-yl)-ethyl]-4,5-dimethoxy-phenylamine (160 mg, 0.4 mmol) was dissolved in 4 mL methylene chloride and 2-tolyl isocyanate (49 μL, 0.4 mmol) was added. The reaction mixtures were stirred at 40° C. overnight. Methylene chloride was added to the vial and the reaction mixture was washed with water. The product was recrystallized in isopropyl alcohol. 1-{2-[2-(4-1,2-Benzisothiazol-3-yl-piperazin-1-yl)-ethyl]-4,5-dimethoxy-phenyl}-3-o-tolyl-urea (168 mg) was isolated in 100% purity @ 254 nm; LCMS (APCI): 532 [M+H]+; mp 200° C.; 1H NMR (400 MHz, CDCl3) δ 8.20 (s, 1H), 7.87 (d, J=8 Hz, 1H), 7.80 (m, 2H), 7.47 (t, 1H), 7.33 (t, 1H), 7.18 (t, 1H), 7.11 (m, 2H), 7.02 (t, 1H), 6.74 (s, 1H), 6.35 (s, 1H), 3.88 (s, 3H), 3.87 (s, 3H), 3.61 (t, 4H), 2.77 (m, 2H), 2.73 (m, 4H), 2.67 (m, 2H), 2.12 (s, 3H).

Workup

customThe reaction mixtures
washwas washed with water
customThe product was recrystallized in isopropyl alcohol

Sources & evidence

ORD record: ord-9d428072f9914f44a25123ab0c5409dd
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101886B2

Reaction notes

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