Diethyl Ether → HCID 21911771, compound

HRID 2217167Notes

Reaction equation

HRID 2217167 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:5]=2[N:6]=1.C(OCC)C.C(=O)(O)[O-].[Na+].[Cl:22][CH2:23][C:24](Cl)=[O:25]>C(OCC)(=O)C>[Cl:22][CH2:23][C:24]([NH:11][C:8]1[CH:9]=[CH:10][C:4]2[S:3][C:2]([CH3:1])=[N:6][C:5]=2[CH:7]=1)=[O:25]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6577Chloroacetyl chlorideHCID 362295-Benzothiazolamine, 2-methyl-HCID 516892Sodium Bicarbonate

Product 1

HCID 21911771HCID 21911771, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Methylbenzothiazole-5-ylamine (1.0 g, 4.2 mm) was suspended in a mixture of 1:1 ethyl ether: saturated aqueous sodium bicarbonate. To the suspension was added chloracetyl chloride (0.7 g, 6.5 mm) over a period of 10 minutes. The mixture was allowed to stir at room temperature for 24 hours, and then diluted with 50 ml of ethyl acetate. The organic layer was separated, dried over magnesium sulgate, and filtered. The solvent was evaporated from the filtrate, and the white solid residue obtained was triturated in ether and filtered, to afford 2-chloro-N-(2-methylbenzothiazol-5-yl)acetamide, a compound of formula (1).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over magnesium sulgate
  3. filtrationfiltered
  4. customThe solvent was evaporated from the filtrate
  5. customthe white solid residue obtained
  6. customwas triturated in ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-0d1042683fbe4e339d3357e430346896
Source dataset
uspto-grants-2008_08
Patent number
US07407960B2

Reaction notes

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