Benzenesulfonyl chloride → HCID 12297945, compound

HRID 1730644Notes

Reaction equation

HRID 1730644 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([CH3:12])[C:9]([NH:13][C:14](=[O:16])[CH3:15])=[C:8]([CH3:17])[C:3]=1[C:4]([NH:6][NH2:7])=[O:5].[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>[OH-].[Na+]>[NH2:1][C:2]1[N:11]=[C:10]([CH3:12])[C:9]([NH:13][C:14](=[O:16])[CH3:15])=[C:8]([CH3:17])[C:3]=1[C:4]([NH:6][NH:7][S:24]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:26])=[O:25])=[O:5]

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 12297944HCID 12297944, compound

Product 1

HCID 12297945HCID 12297945, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-amino-5-acetamido-4,6-dimethylnicotinic acid hydrazide (34.4 g., 0.145 mole) in 1N sodium hydroxide solution (348 ml.) is added at ambient temperature and with vigorous stirring, benzenesulfonyl chloride (31.1 g., 0.16 mole) in one portion. After about three-quarters of an hour the acid chloride disappears; the maximum temperature attained by the reaction mixture, 36° C. The product is precipitated by pouring the reaction mixture into a stirred solution of acetic acid (8.3 ml.) in water (250 ml.). It is collected, slurried with water (150 ml.), refiltered and dried affording 49.52 g. (90%) of crude product, m.p. 216°-218° C. with gas evolution. Following purification by dissolving in hot (100° C.) dimethylformamide, filtering, and diluting with methanol (1 part) and water (3 parts) the product melts at 233°-234° C. (dec.).

Workup

  1. customabout three-quarters of an hour
  2. customattained by the reaction mixture, 36° C
  3. customThe product is precipitated
  4. additionby pouring the reaction mixture into a stirred solution of acetic acid (8.3 ml.) in water (250 ml.)
  5. customIt is collected
  6. customdried
  7. customaffording 49.52 g
  8. custompurification
  9. dissolutionby dissolving in hot (100° C.) dimethylformamide
  10. filtrationfiltering
  11. additiondiluting with methanol (1 part) and water (3 parts) the product melts at 233°-234° C. (dec.)

Sources & evidence

ORD record
ord-298a4fe00c6146d5b8755cdf762e77a4
Source dataset
uspto-grants-1976_11
Patent number
US03993656

Reaction notes

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