Aniline → 2-Ethyl-4-hydroxy-N-phenyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide

HRID 1730563Notes

Reaction equation

HRID 1730563 reaction equation
C[O:2][C:3]([C:5]1[N:6]([CH2:22][CH3:23])[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.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1(C)C(C)=CC=CC=1>[CH2:22]([N:6]1[C:5]([C:3]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:2])=[C:10]([OH:11])[C:9]2[CH:12]=[CH:13][C:14]3[C:19]([C:8]=2[S:7]1(=[O:21])=[O:20])=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH3:23]

Participants

4

Reactant 2

HCID 6115AnilineHCID 681427532-Ethyl-4-hydroxy-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxylic acid methyl ester-1,1-dioxide

Product 1

HCID 546959402-Ethyl-4-hydroxy-N-phenyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture consisting of 1.65 gm (5 millimols) of 2-ethyl-4-hydroxy-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxylic acid methyl ester -1,1-dioxide, 0.56 gm (6 millimols) of aniline and 150 ml of anhydrous xylene was refluxed for 24 hours in a Soxhlet apparatus equippedwith a 4-A-molecular sieve. After cooling, 1.8 gm (90% of theory) of 2-ethyl-4-hydroxy-N-phenyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide, m.p. 245°-247° C (from xylene), crystallized out of the reaction mixture.

Workup

  1. temperaturewas refluxed for 24 hours in a Soxhlet apparatus equippedwith a 4-A-molecular sieve
  2. temperatureAfter cooling
  3. custom1.8 gm (90% of theory) of 2-ethyl-4-hydroxy-N-phenyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide, m.p. 245°-247° C (from xylene), crystallized out of the reaction mixture

Sources & evidence

ORD record
ord-5f82c6a116994509b3fbe8aada9a5266
Source dataset
uspto-grants-1976_11
Patent number
US03992535

Reaction notes

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