2-Naphthalenecarboxamide, N-[4-[2,4-bis(1,1-dimethylpropyl)phenoxy]butyl]-1-hydroxy- → 2-Naphthalenecarboxamide, N-[4-[2,4-bis(1,1-dimethylpropyl)phenoxy]butyl]-1-hydroxy-4-[(1-phenyl-1H-tetrazol-5-yl)thio]-

HRID 1938875Notes

Reaction equation

HRID 1938875 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH2:29][CH3:30])([CH3:28])[CH3:27])=[CH:22][C:21]=1[C:31]([CH2:34][CH3:35])([CH3:33])[CH3:32])=[O:13].[C:36]1([N:42]2[C:46]([S:47]Cl)=[N:45][N:44]=[N:43]2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(Cl)(Cl)(Cl)Cl>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([S:47][C:46]2[N:42]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:43]=[N:44][N:45]=2)=[CH:4][C:3]=1[C:12]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH2:29][CH3:30])([CH3:27])[CH3:28])=[CH:22][C:21]=1[C:31]([CH2:34][CH3:35])([CH3:33])[CH3:32])=[O:13]

Participants

4

Reactant 2

HCID 1225662-Naphthalenecarboxamide, N-[4-[2,4-bis(1,1-dimethylpropyl)phenoxy]butyl]-1-hydroxy-HCID 109767911H-Tetrazole-5-sulfenyl chloride, 1-phenyl-

Product 1

HCID 787672-Naphthalenecarboxamide, N-[4-[2,4-bis(1,1-dimethylpropyl)phenoxy]butyl]-1-hydroxy-4-[(1-phenyl-1H-tetrazol-5-yl)thio]-Yield 77.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a solution of 47.6 g of 1-hydroxy-N-[4-(2,4-di-t-amylphenoxy)-butyl]-2-naphthamide in 500 ml of carbon tetrachloride, was added a solution of 21 g of 1-phenyl-5-tetrazolylsulfur chloride (prepared according to Org. Synth. Coll., vol. II, page 445) in 200 ml of carbon tetrachloride. The mixture was refluxed overnight and concentrated in vacuo. The solid was recrystallized from 500 ml of acetonitrile, yielding 50 g of 1-hydroxy-4-(1-phenyl-5-tetrazolylthio)-N-[4-(2,4-di-t-amylphenoxy)-butyl]-2-naphthamide of formula ##STR10## which melted at 147°-148° C. (Synthesis as described in U.S. Pat. No. 3,701,783).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. concentrationconcentrated in vacuo
  3. customThe solid was recrystallized from 500 ml of acetonitrile

Sources & evidence

ORD record
ord-214a24d37b024137b3d05458a4cfea0a
Source dataset
uspto-grants-1997_12
Patent number
US05693846

Reaction notes

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