Water → HCID 86646936, compound

HRID 1929341Notes

Reaction equation

HRID 1929341 reaction equation
[OH-].[K+].[NH2:3][C:4]1[S:5][C:6]2[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:7]=2[N:8]=1.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=1[CH2:22]Cl.O>CN(C)C=O>[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=1[CH2:22][O:13][C:11]1[CH:10]=[CH:9][C:7]2[N:8]=[C:4]([NH2:3])[S:5][C:6]=2[CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 334622-Amino-6-benzothiazololHCID 1086751-Chloro-2-(chloromethyl)-3-fluorobenzene

Product 1

HCID 86646936HCID 86646936, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

add 337 mg of anhydrous potassium hydroxide to a solution of 1 g of 2-amino-1,3-benzothiazol-6-ol in 5 cm3 of N,N-dimethylformamide. After stirring for one hour at a temperature close to 20° C., a solution of 1.08 g of 1-chloro-2-(chloromethyl)-3-fluorobenzene in 2 cm3 of N,N-dimethylformamide is added dropwise. Stir the resultant mixture for about twenty hours at about 20° C. The reaction mixture is poured into 30 cm3 of water, and extracted three times with 50 cm3 of dichloromethane. The organic phases are combined and washed three times with 50 cm3 of a 0.1N aqueous solution of sodium hydroxide, then dried over magnesium sulphate, filtered and concentrated under reduced pressure (0.2 kPa). The residue is taken up in 10 cm3 of a dichloromethane/methanol mixture (98/2 by volume), drained and then washed twice with 5 cm3 of the same mixture, stove-dried under reduced pressure (0.2 kPa) and at a temperature close to 35° C. We obtain 339 mg of 6-[(2-chloro-6-fluorobenzyl)oxy]-1,3-benzothiazol-2-amine in the form of a white solid, which has the following characteristics:

Workup

  1. customclose to 20° C.
  2. extractionextracted three times with 50 cm3 of dichloromethane
  3. washwashed three times with 50 cm3 of a 0.1N aqueous solution of sodium hydroxide
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure (0.2 kPa)
  7. washwashed twice with 5 cm3 of the same mixture
  8. customstove-dried under reduced pressure (0.2 kPa) and at a temperature
  9. customclose to 35° C

Sources & evidence

ORD record
ord-24110ace145e4595832d0dd8f78f9dd7
Source dataset
uspto-grants-2012_05
Patent number
US08188078B2

Reaction notes

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