Dimethylformamide dimethyl acetal → 3-(3-Benzyl-5-dimethylaminomethylene-4-oxothiazolidin-2-ylideneamino)-4-ethylamino-benzonitrile

HRID 600825Notes

Reaction equation

[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][S:10][C:9]1=[N:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[NH:23][CH2:24][CH3:25])[C:18]#[N:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[CH:28](OC)[N:29]([CH3:31])[CH3:30]>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[CH:28][N:29]([CH3:31])[CH3:30])[S:10][C:9]1=[N:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[NH:23][CH2:24][CH3:25])[C:18]#[N:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 125 °C

Procedure

To a solution of 3-(3-benzyl-4-oxothiazolidin-2-ylideneamino)-4-ethylamino-benzonitrile (84 mg, 0.24 mmol) in toluene (1.0 mL, anhyd) was added N,N-dimethylformamide dimethyl acetal (1.0 mL, 7.5 mmol). The reaction mixture was heated at 125° C. After 20 h, the mixture was cooled and chromatographed (silica gel, DCM) to afford the title product (60 mg, 62%) as a pale yellow solid. 1H-NMR (CDCl3): δ 7.60 (1H, s), 7.24-7.40 (6H, m), 7.15 (1H, d), 6.46 (1H, d), 5.09 (2H, s), 4.14 (1H, br t), 3.12 (6H, s), 2.98 (2H, m), 0.99 (3H, t); MS (ESI): 406 (MH+).

Workup

temperaturethe mixture was cooled
customchromatographed (silica gel, DCM)

Sources & evidence

ORD record: ord-113d0686b860483a888329d7f02a0a4f
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902237B2

Reaction notes

Loading…