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Benzenethiol, 2-amino-, hydrochloride (1:1) → Ethyl 2-[4-(benzothiazol-2-yl)methyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl]acetate

HRID 1655894
Notes
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Reaction equation

HRID 1655894 reaction equation
[C:1]([CH2:3][N:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[S:7][CH:6]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:5]1=[O:20])#[N:2].Cl.N[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[SH:29]>O>[S:29]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:2]=[C:1]1[CH2:3][N:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[S:7][CH:6]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:5]1=[O:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 76794Benzenethiol, 2-amino-, hydrochloride (1:1)HCID 10062806Ethyl 2-(4-cyanomethyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl)acetate

Product 1

HCID 9978204Ethyl 2-[4-(benzothiazol-2-yl)methyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl]acetateYield 68.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 208 mg of ethyl 2-(4-cyanomethyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl)acetate and 116 mg of 2-aminothiophenol hydrochloride was heated at 180° C. for 15 minutes to fuse them. After the mixture had been cooled, water was added, and then extracted with ethyl acetate. After the drying of the organic layer over anhydrous magnesium sulfate, the solvent was distilled off. The resulting oily matter was purified by silica gel chromatography to give 196 mg of the title compound. The structural formula and physical data of this compound are shown in Table 15.

Workup

  1. temperatureAfter the mixture had been cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialAfter the drying of the organic layer over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe resulting oily matter was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c897ccbf25c14139924b6ecfb0f78c98
Source dataset
uspto-grants-1993_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05252571

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes