Ethanol → Benzothiazole, 5,6-dimethoxy-2-methyl-

HRID 1881174Notes

Reaction equation

HRID 1881174 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[N+:12]([O-])=O.[S-2:15].[Na+].[Na+].[S].[CH2:19](O)[CH3:20]>>[CH3:11][O:10][C:5]1[C:6]([O:8][CH3:9])=[CH:7][C:2]2[S:15][C:19]([CH3:20])=[N:12][C:3]=2[CH:4]=1

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 14804Sodium SulfideHCID 1709684-Bromo-5-nitroveratroleHCID 5362487Sulfur

Product 1

HCID 112829Benzothiazole, 5,6-dimethoxy-2-methyl-

Procedure

1-Bromo-4,5-dimethoxy-2-nitro-benzene (10 g) was suspended into ethanol (50 ml). To the reaction mixture was added the suspension of sodium sulfide (5 g) and sulfur (0.65 g) in ethanol (12 ml). The reaction mixture was refluxed 1.5 hour and then the resultant solid was filtered and washed with hot water and ethanol. The dry solid was slurried with acetic acid (60 ml) and acetanhydridi (35 ml). To the suspension was gradually added zinc (16.6 g) and the suspension was stirred at room temperature for 15 min before filtering off. The residue was evaporated to dryness. The product was purified by column chromatography using toluene-ethyl acetate-acetic acid 8:1:1 as the eluent.

Workup

  1. additionTo the reaction mixture was added
  2. temperatureThe reaction mixture was refluxed 1.5 hour
  3. filtrationthe resultant solid was filtered
  4. washwashed with hot water and ethanol
  5. filtrationbefore filtering off
  6. customThe residue was evaporated to dryness
  7. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-e2b8445e6e684076841356a2e6169893
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

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