Sulfanilamide → 3-(1-Dimethylaminoethylidene)-5-(oxazol-5-yl)-1,3-dihydroindol-2-one

HRID 840842Notes

Reaction equation

HRID 840842 reaction equation
O1C(C2C=C3C(=CC=2)NC(=O)C3)=CN=C1.COC(OC)(N(C)C)C.[CH3:25][N:26]([CH3:44])[C:27](=[C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([C:38]3[O:42][CH:41]=[N:40][CH:39]=3)[CH:36]=2)[NH:31][C:30]1=[O:43])[CH3:28].[S:45]([NH2:55])(=[O:54])([C:47]1[CH:52]=[CH:51][C:50]([NH2:53])=[CH:49][CH:48]=1)=[O:46]>>[CH3:44][N:26]([CH3:25])[C:27](=[C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([C:38]3[O:42][CH:41]=[N:40][CH:39]=3)[CH:36]=2)[NH:31][C:30]1=[O:43])[CH3:28].[O:42]1[C:38]([C:35]2[CH:36]=[C:37]3[C:32](=[CH:33][CH:34]=2)[NH:31][C:30](=[O:43])[C:29]3=[C:27]([NH:53][C:50]2[CH:49]=[CH:48][C:47]([S:45]([NH2:55])(=[O:54])=[O:46])=[CH:52][CH:51]=2)[CH3:28])=[CH:39][N:40]=[CH:41]1

Participants

6

Reactant 4

HCID 5333SulfanilamideHCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 110089415-(Oxazol-5-yl)-1,3-dihydroindol-2-oneHCID 571840423-(1-Dimethylaminoethylidene)-5-(oxazol-5-yl)-1,3-dihydroindol-2-one

Product 2

HCID 571840423-(1-Dimethylaminoethylidene)-5-(oxazol-5-yl)-1,3-dihydroindol-2-oneHCID 1784633264-[1-[5-(1,3-oxazol-5-yl)-2-oxo-1H-indol-3-ylidene]ethylamino]benzenesulfonamide

Procedure

3-(1-Dimethylaminoethylidene)-5-(oxazol-5-yl)-1,3-dihydroindol-2-one was prepared from 5-(oxazol-5-yl)-1,3-dihydroindol-2-one and N,N-dimethylacetamide dimethyl acetal according to Procedure H. Condensation of 3-(1-dimethylaminoethylidene)-5-(oxazol-5-yl)-1,3-dihydroindol-2-one and sulfanilamide according to Procedure J provided the title compound: mp>250° C.; 1H NMR (DMSO-d6): δ2.51 (s, 0.8H, DMSO), 2.61 (s, 3H), 6.97 (d, J=8.2 Hz, 1H), 7.37 (s, 2H), 7.40 (dd, J=8.0, 1.5 Hz, 1H), 7.45 (d, J=8.8 Hz, 2H), 7.56 (s, 1H), 7.66 (d, J=1.2 Hz,1H), 7.83 (d, J=8.5 Hz, 2H), 8.34 (s, 1H), 10.85 (s, 1H), 12.33 (s, 1H); APCI−MS m/z 395 (M−H)−. Anal. Calcd for C19H16N4O4S.0.1C2H6OS.0.6H2O: C, 55.56; H, 4.32; N, 13.50; S, 8.50. Found: C, 55.53; H, 4.32; N, 13.27; S, 8.58.

Sources & evidence

ORD record
ord-841f17bad70140aebf80b1d5e1fe0851
Source dataset
uspto-grants-2002_04
Patent number
US06369086B1

Reaction notes

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