Chloride → 4-Benzyloxy-2-amino-N-[3-benzyloxy-4-(1-adamantyl)benzoyl]aniline

HRID 1757472Notes

Reaction equation

HRID 1757472 reaction equation
[NH2:1][C:2]1[CH:8]=[C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:3]=1[NH2:4].[Cl-].[CH2:18]([O:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][C:34]=1[C:35]12[CH2:44][CH:39]3[CH2:40][CH:41]([CH2:43][CH:37]([CH2:38]3)[CH2:36]1)[CH2:42]2)[C:29](O)=[O:30])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(OCC)(=O)C.CCCCCC>[CH2:10]([O:9][C:7]1[CH:6]=[CH:5][C:3]([NH:4][C:29](=[O:30])[C:28]2[CH:32]=[CH:33][C:34]([C:35]34[CH2:36][CH:37]5[CH2:38][CH:39]([CH2:40][CH:41]([CH2:43]5)[CH2:42]3)[CH2:44]4)=[C:26]([O:25][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:27]=2)=[C:2]([NH2:1])[CH:8]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 312ChlorideHCID 131622394-(Benzyloxy)benzene-1,2-diamineHCID 178670343-Benzyloxy-4-(1-adamantyl)benzoic acid

Product 1

HCID 193879974-Benzyloxy-2-amino-N-[3-benzyloxy-4-(1-adamantyl)benzoyl]aniline

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

2.7 g (12.7 mM) of 2-amino-4-(benzyloxy)aniline and 5 g (12.7 mM) of the chloride of 3-benzyloxy-4-(1-adamantyl)benzoic acid are treated under the conditions described in Example 1(f) to lead, after the same treatment andchromatography on silica in the ethyl acetate/hexane (30/70) eluent, to 4.2g (59.3%) of the expected derivative, of melting point 178° C.

Sources & evidence

ORD record
ord-80dc34528c724dc8bde4c17d3c45284a
Source dataset
uspto-grants-1995_08
Patent number
US05446059

Reaction notes

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