Oxalyl chloride → N-[5-(2,4-dioxothiazolidin-5-yl)methyl-2-hydroxyphenyl]-2-(4-dimethylaminophenyl)acetamide

HRID 330480Notes

Reaction equation

HRID 330480 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[OH:16])[CH2:5][CH:6]1[S:10][C:9](=[O:11])[NH:8][C:7]1=[O:12].[CH3:17][N:18]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](Cl)=[O:28])=[CH:22][CH:21]=1)[CH3:19].CN(C1C=CC(CC(O)=O)=CC=1)C.C(Cl)(=O)C(Cl)=O>>[O:11]=[C:9]1[NH:8][C:7](=[O:12])[CH:6]([CH2:5][C:4]2[CH:13]=[CH:14][C:15]([OH:16])=[C:2]([NH:1][C:27](=[O:28])[CH2:26][C:23]3[CH:24]=[CH:25][C:20]([N:18]([CH3:19])[CH3:17])=[CH:21][CH:22]=3)[CH:3]=2)[S:10]1

Participants

5

Reactant 4

HCID 65578Oxalyl chlorideHCID 1522034-N,N-dimethylaminophenylacetic acidHCID 104901085-(3-Amino-4-hydroxybenzyl)-2,4-dioxothiazolidineHCID 147235052-(4-(Dimethylamino)phenyl)acetyl chloride

Product 1

HCID 10787103N-[5-(2,4-dioxothiazolidin-5-yl)methyl-2-hydroxyphenyl]-2-(4-dimethylaminophenyl)acetamide

Procedure

5-(3-amino-4-hydroxybenzyl)-2,4-dioxothiazolidine and 4-(N,N-dimethylamino)phenylacetyl chloride, prepared from 4-(N,N-dimethylamino)phenylacetic acid and oxalyl chloride, are treated in the same manner as described in Example 5-(1) to give N-[5-(2,4-dioxothiazolidin-5-yl)methyl-2-hydroxyphenyl]-2-(4-dimethylaminophenyl)acetamide.

Workup

  1. additionare treated in the same manner

Sources & evidence

ORD record
ord-55b44d8767cd4a2981c4cfecaa5ec080
Source dataset
uspto-grants-1990_01
Patent number
US04897393

Reaction notes

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