1-Amino-2-naphthalenethiol → 3-(4-chlorophenyl)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one

HRID 5828

Reaction equation

HRID 5828 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[SH:12].[BH4-].[Na+].C([O-])(=O)C.[Na+].Br[CH:21]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)[C:22](OC)=[O:23]>C(O)C.C(O)(=O)C>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([CH:21]2[S:12][C:3]3[CH:4]=[CH:5][C:6]4[C:11]([C:2]=3[NH:1][C:22]2=[O:23])=[CH:10][CH:9]=[CH:8][CH:7]=4)=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 1133141-Amino-2-naphthalenethiolHCID 517045Sodium AcetateHCID 4311764Sodium borohydrideHCID 10777987Methyl 2-bromo-2-(4-chlorophenyl)acetate

Product 1

HCID 189844403-(4-chlorophenyl)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-oneYield 86%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of 1-amino-2-naphthalenethiol (27.81 g) in ethanol (500 ml) is added sodium borohydride (11.35 g) at room temperature. The mixture is stirred for 20 minutes, and thereto is added dropwise acetic acid (200 ml) and is further added sodium acetate (24.6 g). To the mixture is further added dropwise methyl α-bromo-4-chlorophenylacetate (46.8 g), and the mixture is sitrred at room temperature under argon overnight. The reaction mixture is poured into ice water and the resulting precipitate is separated by filtration, washed, dried and recrystallized from tetrahydrofuran-n-hexane to give 3-(4-chlorophenyl)-1H-naphtho-[2,1-b][1,4]thiazin-2(3H)-one (44.45 g, yield 82.6%) as crystals.

Workup

  1. waitthe mixture is sitrred at room temperature under argon overnight
  2. customthe resulting precipitate is separated by filtration
  3. washwashed
  4. customdried
  5. customrecrystallized from tetrahydrofuran-n-hexane

Sources & evidence

ORD record
ord-d1e1ce17b0b34812b37a771e23bf789c
Source dataset
uspto-grants-1993_09
Patent number
US05246929

Linked notes

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