Methanesulfonic Acid → HCID 971448, compound

HRID 728996Notes

Reaction equation

HRID 728996 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[OH:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](O)=O)=[CH:12][C:11]=1[N+:19]([O-:21])=[O:20].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.CS(O)(=O)=O.C(=O)(O)[O-].[Na+].[OH-].[Na+]>>[S:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:14]1[C:13]1[CH:17]=[CH:18][C:10]([OH:9])=[C:11]([N+:19]([O-:21])=[O:20])[CH:12]=1

Participants

7

Reactant 6

HCID 6395Methanesulfonic AcidHCID 87132-AminothiophenolHCID 120334-Hydroxy-3-nitrobenzoic acidHCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 516892Sodium Bicarbonate

Product 1

HCID 971448HCID 971448, compoundYield 20.2%

Conditions

Temperature
90 °C

Procedure

A mixture of 14.8 g 2-aminothiophenol, 21.6 g 4-hydroxy-3-nitrobenzoic acid, 18 g phosphorus pentoxide and 180 g methanesulfonic acid was heated at 90° C. for 10 hours. The reaction mixture was brought to pH 5 byaddition of sodium bicarbonate and sodium hydroxide solutions, and the solid product collected. The latter was recrystallized first from ethyl acetate and then from acetonitrile to give 6.5 g of the above-indicated product, orange-brown needles, m.p. 214°-215° C.

Workup

  1. customthe solid product collected
  2. customThe latter was recrystallized first from ethyl acetate

Sources & evidence

ORD record
ord-98cedfeeccf84372a24ebc456c30b025
Source dataset
uspto-grants-1991_09
Patent number
US05051437

Reaction notes

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