Methyl Ethyl Ketone → HCID 86739836, compound

HRID 1154510Notes

Reaction equation

HRID 1154510 reaction equation
Cl[C:2]1[CH:7]=C[C:5]([CH:8]=[C:9]2[C:14](=O)[NH:13][C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[S:10]2)=[CH:4][CH:3]=1.[OH-:20].[Na+].[ClH:22].Cl[CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.[CH2:32](C(C)=O)C>>[Cl:22][C:3]1[CH:2]=[CH:7][C:8]([CH:9]2[C:14](=[O:20])[N:13]([CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[S:10]2=[CH2:32])=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 14798Sodium HydroxideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 2826591HCID 2826591, compound

Product 1

HCID 86739836HCID 86739836, compound

Procedure

2-(4-Chlorophenylmethylidene)-2H-1,4-benzothiazine-3(4H)-one (2.0 g) was reacted with sodium hydroxide (0.72 g) in methyl ethyl ketone (20 ml) at 80° C. for 30 minutes. After the solution turned clear, it was cooled to room temperature. N-(2-chloroethyl)morpholine hydrochloride (1.7 g) was added to the mixture. The organic solvent was evaporated under reduced pressure. The resulted yellow solid was filtered and washed with water and with methanol. It was recrystallized from a mixture of dimethylformamide and isopropyl alcohol. 2-(4-Chlorophenyl)-methylidene-4-(2-morpholinoethyl)-2H-1,4-benzothiazine-3(4H)-one (2.0 g) was obtained as yellow crystals, m.p. 173° to 175° C.

Workup

  1. customThe organic solvent was evaporated under reduced pressure
  2. filtrationThe resulted yellow solid was filtered
  3. washwashed with water and with methanol
  4. customIt was recrystallized from a mixture of dimethylformamide and isopropyl alcohol

Sources & evidence

ORD record
ord-5ea74725cb7148baa5e7350714fafd96
Source dataset
uspto-grants-1984_12
Patent number
US04490292

Reaction notes

Loading…