Aniline → HCID 54695934, compound

HRID 1730558Notes

Reaction equation

HRID 1730558 reaction equation
CO[C:3]([C:5]1[NH:6][S:7](=[O:21])(=[O:20])[C:8]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][C:9]=2[C:10]=1[OH:11])=[O:4].[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1(C)C(C)=CC=CC=1>[OH:11][C:10]1[C:9]2[CH:12]=[CH:13][C:14]3[C:19]([C:8]=2[S:7](=[O:21])(=[O:20])[NH:6][C:5]=1[C:3]([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:4])=[CH:18][CH:17]=[CH:16][CH:15]=3

Participants

4

Reactant 2

HCID 6115AnilineHCID 547193904-hydroxy-2H-naphtho[2,1-e]-1,2thiazine-3-carboxylic acid methyl ester-1,1-dioxide

Product 1

HCID 54695934HCID 54695934, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 9.58 gm (0.03 mol) of 4-hydroxy-2H-naphtho[2,1-e]-1,2thiazine-3-carboxylic acid methyl ester-1,1-dioxide, 3.72 gm (0.04 mol) of aniline and 150 ml of anhydrous xylene was refluxed for 10 hours in a Soxhlet apparatus equipped with a 4-A-molecular sieve. After cooling, the reaction mixture was allowed to stand overnight, whereupon the precipitaed crystals were suction-filtered off and recrystallized from ethylene chloride. 6.10 gm (55% of theory) of 4-hydroxy-N-phenyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide, m.p. 260°-262° C, were obtained.

Workup

  1. temperaturewas refluxed for 10 hours in a Soxhlet apparatus
  2. customequipped with a 4-A-molecular sieve
  3. temperatureAfter cooling
  4. filtrationwere suction-filtered off
  5. customrecrystallized from ethylene chloride

Sources & evidence

ORD record
ord-31f90da446e349ce8268535923cd984b
Source dataset
uspto-grants-1976_11
Patent number
US03992535

Reaction notes

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