Acetic Acid → HCID 12275049, compound

HRID 1730651Notes

Reaction equation

HRID 1730651 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([C:16]([F:19])([F:18])[F:17])[C:3]=1[C:4]([NH:6][NH2:7])=[O:5].[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O)(=O)C.C(Cl)(Cl)Cl>[OH-].[Na+].O.C(OCC)(=O)C>[NH2:1][C:2]1[N:11]=[C:10]([C:12]([F:13])([F:14])[F:15])[CH:9]=[C:8]([C:16]([F:19])([F:17])[F:18])[C:3]=1[C:4]([NH:6][NH:7][S:26]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:28])=[O:27])=[O:5]

Participants

8

Reactant 4

HCID 176Acetic Acid2×HCID 6212ChloroformHCID 7369Benzenesulfonyl chlorideHCID 122750483-Pyridinecarboxylic acid, 2-amino-4,6-bis(trifluoromethyl)-, hydrazide

Product 1

HCID 12275049HCID 12275049, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

2-Amino-4,6-di(trifluoromethyl)-nicotinic acid hydrazide (4.35 g., 15.1 mmole) is stirred in 1N sodium hydroxide solution (36.3 ml.) untila clear solution is obtained. Benzenesulfonyl chloride (2.94 g., 16.6 mmole) is added in one portion and the mixture stirred rapidly until solution is complete. On pouring this solution into a stirred solution of acetic acid (0.9 g., 15 mmole) in water (40 ml.), a fine precipitate is formed. The pH of the suspension is adjusted to circa 6.5 with acetic acid and the product collected, washed with water and dried giving 6.52 g. (theoretical) of product sintering at circa 230° C., m.p. 235°-238° C. (dec.). The product is obtained pure by precipitation from a filtered solution of the crude product in ethyl acetate (4 parts volume by weight) by addition of chloroform (10 parts volume by weight) providing product with m.p. 243°-245° C. (dec.).

Workup

  1. customis obtained
  2. customa fine precipitate is formed
  3. customthe product collected
  4. washwashed with water
  5. customdried
  6. customgiving 6.52 g
  7. customat circa 230° C.

Sources & evidence

ORD record
ord-7de31fbcfb1f42bcb8e18fff3fbe5681
Source dataset
uspto-grants-1976_11
Patent number
US03993656

Reaction notes

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