Acetic Acid → HCID 18626168, compound

HRID 1859672Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH:5]=O.[NH2:11][C:12]1[CH:13]=[C:14]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[C:15]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:16].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH2:5][NH:11][C:12]1[CH:13]=[C:14]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[C:15]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:16]

Participants

Reactant 4

HCID 176Acetic Acid

HCID 84263-Amino-4-methoxybenzanilide

HCID 357463,5-Dichlorobenzaldehyde

HCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18626168HCID 18626168, compoundYield 32.4%

Procedure

Prepared according to the procedure of Example 50 using 3,5-dichloro-benzaldehyde (0.88 g, 5.0 mmol), 3-amino-4-methoxy-N-phenyl-benzamide (1.22 g, 5.0 mmol), acetic acid (0.24 g, 5.3 mmol), and sodium triacetoxyborohydride (1.12 mmol) to afford the product (0.65 g); m.p. 164-165° C. after recrystallization from ethanol.

Workup

customPrepared

Sources & evidence

ORD record: ord-d3c899898ded4a3197861d8ea47b88b6
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528528B2

Reaction notes

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