P-Anisidine → HCID 136409738, compound

HRID 972438Notes

Reaction equation

HRID 972438 reaction equation
[CH2:1]([S:17]([NH:20][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:30]=1[CH:29]=[C:28]([OH:31])[CH:27]=[CH:26]2)(=[O:19])=[O:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[OH-].[Na+].[CH3:34][O:35][C:36]1[CH:41]=[CH:40][C:39]([NH2:42])=[CH:38][CH:37]=1.[N:43]([O-])=O.[Na+]>O.O1CCCC1.CO>[CH2:1]([S:17]([NH:20][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:30]=1[C:29]([N:43]=[N:42][C:39]1[CH:40]=[CH:41][C:36]([O:35][CH3:34])=[CH:37][CH:38]=1)=[C:28]([OH:31])[CH:27]=[CH:26]2)(=[O:18])=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

8

Reactant 4

HCID 7732P-AnisidineHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 54062299HCID 54062299, compound

Product 1

HCID 136409738HCID 136409738, compoundYield 92.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 89.5 g (0.20 mole) 8-hexadecanesulfonamido-2-naphthol, 37 g sodium hydroxide, 1800 ml methanol, and 1200 ml tetrahydrofuran at 0° was added a diazonium salt solution prepared from 24.6 g (0.20 mole) p-anisidine dissolved in 360 ml water containing 60 ml concentrated hydrochloric acid and a solution of 13.8 g (0.20 mole) sodium nitrite in 240 ml water. The addition required 15 min., and the mixture was stirred at 0° for 0.5 hr. and at room temperature for 0.5 hr. longer before being poured into 6 liters of water containing 250 ml acetic acid. There was obtained 107.7 g of product.

Workup

  1. additionThe addition required 15 min.
  2. waitand at room temperature for 0.5 hr

Sources & evidence

ORD record
ord-448d136eddf5489dae4e28eec75acd14
Source dataset
uspto-grants-1977_10
Patent number
US04053312

Reaction notes

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