P-Anisidine → HCID 135727397, compound

HRID 972435Notes

Reaction equation

HRID 972435 reaction equation
[CH2:1]([N:13]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[S:14]([C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([OH:27])=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[OH-].[Na+].[CH3:42][O:43][C:44]1[CH:49]=[CH:48][C:47]([NH2:50])=[CH:46][CH:45]=1.[N:51]([O-])=O.[Na+]>O1CCCC1.O.CO>[CH2:28]([N:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[S:14]([C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([OH:27])=[C:19]([N:51]=[N:50][C:47]2[CH:48]=[CH:49][C:44]([O:43][CH3:42])=[CH:45][CH:46]=2)[CH:18]=1)(=[O:16])=[O:15])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Participants

8

Reactant 4

HCID 7732P-AnisidineHCID 14798Sodium HydroxideHCID 21404066HCID 21404066, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 135727397HCID 135727397, compoundYield 77.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 30.7 g (0.027 mole) crude 4-(N,N-didodecylsulfamyl)-1-naphthol in a mixture of 100 ml tetrahydrofuran, 100 ml methanol, and 4.2 ml 50% sodium hydroxide solution was cooled in an ice-acetone bath and treated with a diazonium salt solution prepared from 3.30 g (0.027 mole) p-anisidine in 20 ml water containing 4.5 ml concentrated hydrochloric acid and 1.85 g (0.027 mole) sodium nitrite in 5 ml of water. The mixture was stirred at 0°-10° C. for 2 hr., allowed to warm to room temperature, and filtered to give 14.6 g of red brown solid. This solid was recrystallized from hexane to give 8.2 g of a bright red powder, m.p. 100°-102° C.

Workup

  1. temperaturewas cooled in an ice-acetone bath
  2. filtrationfiltered

Sources & evidence

ORD record
ord-5fd47313b4a74d2a944f9aac8a3ebf71
Source dataset
uspto-grants-1977_10
Patent number
US04053312

Reaction notes

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