Benzaldehyde → (Z)-3-(2-(dibenzylamino)ethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

HRID 517588Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])/[C:7](=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[CH:13][CH:12]=2)/[S:6][C:5]1=[O:20].[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O[C:46]1[CH:63]=[CH:62][C:49](/[CH:50]=C2/C(=O)N(CCNC)C(=O)S/2)=[CH:48][CH:47]=1)C>>[CH2:21]([N:1]([CH2:50][C:49]1[CH:62]=[CH:63][CH:46]=[CH:47][CH:48]=1)[CH2:2][CH2:3][N:4]1[C:8](=[O:9])/[C:7](=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[CH:13][CH:12]=2)/[S:6][C:5]1=[O:20])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Reactant 4

HCID 240Benzaldehyde

HCID 1249836(Z)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

HCID 5049666Sodium triacetoxyborohydride

HCID 71697257(Z)-5-(4-ethoxybenzylidene)-3-(2-(methylamino)ethyl)thiazolidine-2,4-dione

Product 1

HCID 71697350(Z)-3-(2-(dibenzylamino)ethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

Procedure

The title compound 24b was prepared from compound 76 (117 mg, 0.40 mmol), benzaldehyde (82 μL, 0.80 mmol) and sodium triacetoxyborohydride (254 mg, 1.20 mmol) in a manner similar to that described for 23a in 93.1% (176 mg) yield as a light-yellow solid.

Workup

customyield as a light-yellow solid

Sources & evidence

ORD record: ord-bda817e58a284208a0195c26b410c865
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115122B2

Reaction notes

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