HCID 15158800, compound → HCID 15158801, compound

HRID 974446Notes

Reaction equation

HRID 974446 reaction equation
[C:1]([N:4]([CH2:17][CH2:18][O:19][C:20](=[C:28]1[CH:35]2[CH2:36][CH:31]3[CH2:32][CH:33]([CH2:37][CH:29]1[CH2:30]3)[CH2:34]2)[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=1)[C:5]([C:7]1[S:8][C:9]2[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:10]=2[N:11]=1)=[O:6])(=[O:3])[CH3:2].[OH:38][C:39]1C=CC2N=C(C(NCCOC(=C3C4CC5CC(CC3C5)C4)C3C=CC=C(O)C=3)=O)SC=2[CH:40]=1>C(OCC)(=O)C.CCCCCC>[C:39]([O:27][C:23]1[CH:22]=[C:21]([C:20](=[C:28]2[CH:35]3[CH2:36][CH:31]4[CH2:32][CH:33]([CH2:37][CH:29]2[CH2:30]4)[CH2:34]3)[O:19][CH2:18][CH2:17][N:4]([C:1](=[O:3])[CH3:2])[C:5]([C:7]2[S:8][C:9]3[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:10]=3[N:11]=2)=[O:6])[CH:26]=[CH:25][CH:24]=1)(=[O:38])[CH3:40]

Participants

4

Reactant 2

HCID 15158800HCID 15158800, compoundHCID 15779975HCID 15779975, compound

Product 1

HCID 15158801HCID 15158801, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The second product was obtained with 35% ethyl acetate/hexane and was found to be {[2-(N-acetyl-N-(6-hydroxybenzothiazole-2-carbonyl)amino)ethoxy][3-hydroxyphenyl]methylene}adamantane (3a): 1H NMR (CDCl3) δ1.80-1.96 (m, 12H), 2.18 (s, 3H), 2.67 (bs, 1H), 3.33 (bs, 1H), 3.65 (m, 4H), 6.74 (bs, 1H), 6.96-7.92 (m, 7H), 7.79 (bs, 1H).; 13C NMR (CDCl3) δ20.97, 28.22, 30.53, 32.35, 37.07, 39.01, 39.14, 39.97, 67.79, 107.09, 117.16, 120.75, 122.35, 125.13, 126.71, 129.10, 133.50, 136.72, 138.86, 140.98, 147.39, 150.65, 155.72, 160.34, 160.43, 169.36. The third product was identified as {[2-(N-(6-hydroxybenzothiazole-2-carbonyl)amino)ethoxy][3-hydroxyphenyl]methylene}adamantane ##STR35##

Sources & evidence

ORD record
ord-2e7ae79ad0684132ae7208f710de81e7
Source dataset
uspto-grants-1991_11
Patent number
US05068339

Reaction notes

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