Potassium Hydroxide → 2-Nitro-5-(6-ethoxybenzothiazol-2-ylthio)aniline

HRID 1981154Notes

Reaction equation

HRID 1981154 reaction equation
[OH-].[K+].[CH2:3]([O:5][C:6]1[CH:15]=[CH:14][C:9]2[N:10]=[C:11]([SH:13])[S:12][C:8]=2[CH:7]=1)[CH3:4].[N+:16]([C:19]1[CH:25]=[CH:24][C:23](Cl)=[CH:22][C:20]=1[NH2:21])([O-:18])=[O:17]>O.CN(C)C=O>[N+:16]([C:19]1[CH:25]=[CH:24][C:23]([S:13][C:11]2[S:12][C:8]3[CH:7]=[C:6]([O:5][CH2:3][CH3:4])[CH:15]=[CH:14][C:9]=3[N:10]=2)=[CH:22][C:20]=1[NH2:21])([O-:18])=[O:17]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 742185-Chloro-2-nitroanilineHCID 178466040HCID 178466040, compound

Product 1

HCID 204000072-Nitro-5-(6-ethoxybenzothiazol-2-ylthio)aniline

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 0.15 moles of potassium hydroxide in a mixture of 15 ml of water and 300 ml of dimethylformamide add 0.15 moles of 6-ethoxybenzothiazole-2-thiol (L. B. Sebrell and C. E. Boord, J. Am. Chem. Soc., 45, 2390 (1923)) under a nitrogen atmosphere. After complete dissolution, add 2-nitro-5-chloroaniline (R. C. Fuson, R. A. Dauman, E. Howard, Jr., and E. N. Marvell, J. Org. Chem., 12, 084 (1947)) and heat the mixture under reflux and a positive nitrogen pressure for about 16 hours. Pour the mixture into 1000 ml of water and remove the resulting precipitate. Wash the precipitate with water and crystallize from acetonitrile to give the title compound having a melting point of 126°-129° C.

Workup

  1. dissolutionAfter complete dissolution
  2. temperature, 12, 084 (1947)) and heat the mixture
  3. temperatureunder reflux
  4. customremove the resulting precipitate
  5. washWash the precipitate with water
  6. customcrystallize from acetonitrile

Sources & evidence

ORD record
ord-aa6c298e0acf425e8bcff07545400b6d
Source dataset
uspto-grants-1985_04
Patent number
US04512998

Reaction notes

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