3-Chloroaniline → N-(3-chloro-phenyl)-4-hydroxy-2H-naphtho[2,1-e]1,2-thiazine-3-carboxamide-1,1-dioxide

HRID 1730559Notes

Reaction equation

HRID 1730559 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].[Cl:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=1)[NH2:26]>C1(C)C(C)=CC=CC=1>[Cl:22][C:23]1[CH:24]=[C:25]([NH:26][C:3]([C:5]2[NH:6][S:7](=[O:20])(=[O:21])[C:8]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:13]=[CH:12][C:9]=3[C:10]=2[OH:11])=[O:4])[CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 547193904-hydroxy-2H-naphtho[2,1-e]-1,2thiazine-3-carboxylic acid methyl ester-1,1-dioxide

Product 1

HCID 54695941N-(3-chloro-phenyl)-4-hydroxy-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 gm (3.3 millimols) of 4-hydroxy-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxylic acid methyl ester-1,1-dioxide, 0.5 gm (4 millimols) of 3-chloroaniline and 200 ml of anhydrous xylene was refluxed for 25 hours in a Soxhlet apparatus equippedwith a 4-A-molecular sieve. Upon cooling, the desired product crystallized out. Yield: 0.9 gm (68% of theory); m.p. 262° C (decomp.).

Workup

  1. temperaturewas refluxed for 25 hours in a Soxhlet apparatus equippedwith a 4-A-molecular sieve
  2. temperatureUpon cooling
  3. customthe desired product crystallized out

Sources & evidence

ORD record
ord-03b518b5688749ff91a70d224b518411
Source dataset
uspto-grants-1976_11
Patent number
US03992535

Reaction notes

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