Acetonitrile → 3-{3-Benzyl-5-[3-methyl-4-methoxy-3H-benzothiazol-2-ylidene]-4-oxothiazolidin-2-ylideneamino}4-ethylaminobenzonitrile

HRID 2122009Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10](SC)[S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.[C:14]1(C)C=CC(S(OC)(=O)=O)=CC=1.CC#N.[CH2:29]([N:36]1[C:40](=[O:41])[CH2:39][S:38][C:37]1=[N:42][C:43]1[CH:44]=[C:45]([CH:48]=[CH:49][C:50]=1[NH:51][CH2:52][CH3:53])[C:46]#[N:47])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1(OC)C=CC=CC=1>[CH2:29]([N:36]1[C:40](=[O:41])[C:39](=[C:10]2[N:9]([CH3:14])[C:8]3[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=3[S:11]2)[S:38][C:37]1=[N:42][C:43]1[CH:44]=[C:45]([CH:48]=[CH:49][C:50]=1[NH:51][CH2:52][CH3:53])[C:46]#[N:47])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a suspension of the 4-methoxy2-methylthiobenzothiazole (0.60 g, 2.8 mmol) in anhydrous anisole (8 mL) was added methyl p-toluenesulfonate (1.4 mL, 9.0 mmol) and the suspension was heated at 130° C. for 3.5 h. After cooling to 20° C., MeCN (5 mL), 3-(3-benzyl-4-oxothiazolidin-2-ylideneamino)-4-ethylaminobenzonitrile (119 mg, 0.34 mmol) and TEA (2.0 mL, 14 mmol) were added. The suspension was stirred for 5 h at 80° C. After cooling to ambient temperature, yellow solids were collected by filtration, washed with MeCN and dried under high vacuum to afford the title compound (123 mg, 69%). 1H-NMR (CDCl3): δ 7.45-7.11 (9H, m), 6.88-6.85 (1H, m), 6.48 (1H, d), 5.17 (2H, s), 4.08 (3H, s), 3.92 (3H, s), 3.02-2.97 (2H, m), 1.02 (3H, t); MS(ESI): 528 (MH+).

Workup

temperatureAfter cooling to 20° C.
temperatureAfter cooling to ambient temperature
filtrationyellow solids were collected by filtration
washwashed with MeCN
customdried under high vacuum

Sources & evidence

ORD record: ord-5d920cc5e57d4f8cafce9425b5ccf552
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06696473B2

Reaction notes

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