4-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-benzaldehyde benzaldehyde → 5-[[4-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)phenyl]methylidene]-2-imino-1,3-thiazolidin-4-one

HRID 1061219Notes

Reaction equation

HRID 1061219 reaction equation
C(=O)C1C=CC=CC=1.[O:9]1[C:13]2([CH2:18][CH2:17][N:16]([C:19]3[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)[O:12][CH2:11][CH2:10]1.COC1C=CC(/C=[C:42]2/[C:43]([NH:45][C:46]([S:48]/2)=[NH:47])=[O:44])=CC=1OC1CCCC1>>[O:9]1[C:13]2([CH2:18][CH2:17][N:16]([C:19]3[CH:26]=[CH:25][C:22]([CH:23]=[C:42]4[S:48][C:46](=[NH:47])[NH:45][C:43]4=[O:44])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)[O:12][CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 222204854-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-benzaldehyde benzaldehydeHCID 137629131(5Z)-5-[(3-cyclopentyloxy-4-methoxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one

Product 1

HCID 1527819965-[[4-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)phenyl]methylidene]-2-imino-1,3-thiazolidin-4-one

Procedure

The title compound was prepared from 4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-benzaldehyde benzaldehyde (Taylor, E. C., Skotnicki, J. S. Synthesis, 1981, 606) and pseudothiohydantoin according to the procedure of Example 35 as an orange solid; 1H NMR (300 MHz, DMSO-d6) δ 1.68 (t, J=5.6 Hz, 4H), 3.43 (t, J=5.6 Hz, 4H), 3.91 (s, 4H), 7.06 (d, J=8.9 Hz, 2H), 7.41 (d, J=8.9 Hz, 2H), 7.48 (s, 1H), 8.99 (brs, 1H), 9.33 (brs, 1H); MS (ES) m/z: 345.9 (MH+); HRMS Calcd. for C17H20N3O3S(MH+): 346.1226. Found: 346.1205. Anal. Calcd. for C17H19N3O3S: C, 59.11; H, 5.54; N, 12.16. Found: C, 58.80; H, 5.71; N, 12.38.

Sources & evidence

ORD record
ord-5cb73e7439a04db5b0a68cd5a8dd3713
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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