Dimethylformamide → 2-Naphthalenecarboxamide, 1-hydroxy-4-[(1-phenyl-1H-tetrazol-5-yl)thio]-N-[2-(tetradecyloxy)phenyl]-

HRID 1938876Notes

Reaction equation

[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](I)=[CH:4][C:3]=1[C:13]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:14].[K].[C:38]1([N:44]2[C:48]([SH:49])=[N:47][N:46]=[N:45]2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.CN(C)C=O>C(O)C>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([S:49][C:48]2[N:44]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[N:45]=[N:46][N:47]=2)=[CH:4][C:3]=1[C:13]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:14]

Participants

Conditions

Temperature: 90 °C

Procedure

1-hydroxy-4-iodo-2'-tetradecyloxy-2-naphthanilide (9 g) and 1-phenyl-5-mercapto-tetrazole potassium salt (3 g) were solubilized im dimethylformamide (25 ml). The solution was heated at 90° C. for 1 hour under stirring. After adding ethanol (25 ml), a white solid precipitated. The solid collected by filtration was crystallized from ethanol. The yield was 90% of 1-hydroxy-4-(1-phenyl-5-tetrazolylthio)-2'-tetradecyloxy-2-naphthanilide of formula ##STR11##

Workup

customa white solid precipitated
filtrationThe solid collected by filtration
customwas crystallized from ethanol

Sources & evidence

ORD record: ord-7803826c6e4f4f55b1da198946df2bf6
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05693846

Reaction notes

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