Benzaldehyde → HCID 71697260, compound

HRID 517585Notes

Reaction equation

HRID 517585 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(OC1C=CC(/C=C2/C(=O)N(CCNC)C(=O)S/2)=CC=1)C>>[CH2:21]([NH: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

5

Reactant 4

HCID 240BenzaldehydeHCID 1249836(Z)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dioneHCID 5049666Sodium triacetoxyborohydrideHCID 71697257(Z)-5-(4-ethoxybenzylidene)-3-(2-(methylamino)ethyl)thiazolidine-2,4-dione

Product 1

HCID 71697260HCID 71697260, compound

Procedure

The title compound 23d was prepared from compound 76 (204 mg, 0.70 mmol), benzaldehyde (71 μL, 0.70 mmol) and sodium triacetoxyborohydride (445 mg, 2.10 mmol) in a manner similar to that described for 23a in 46.0% (123 mg) yield as a light-yellow solid.

Workup

  1. customyield as a light-yellow solid

Sources & evidence

ORD record
ord-1bf91229b8424ad5b8e88fca24918543
Source dataset
uspto-grants-2015_08
Patent number
US09115122B2

Reaction notes

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