Acetic Acid → 2-Chloro-6-ethylaminobenzothiazole

HRID 1511490Notes

Reaction equation

HRID 1511490 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([Cl:9])[S:8][C:4]=2[CH:3]=1.[CH:12](=O)[CH3:13].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClC(Cl)C.O>[Cl:9][C:7]1[S:8][C:4]2[CH:3]=[C:2]([NH:1][CH2:12][CH3:13])[CH:11]=[CH:10][C:5]=2[N:6]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 109212032-Chloro-1,3-benzothiazol-6-amine

Product 1

HCID 670401072-Chloro-6-ethylaminobenzothiazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of (29) (0.2 mmol, 36.8 mg) in 2 ml dichloroethane was added 0.2 mmol acetaldehyde, followed by 63.6 mg sodium triacetoxyborohydride, and 12 μl acetic acid. After 2 h, the solution was poured into water and extracted with ethyl acetate. The combined extracts were washed with water, dried over sodium sulfate, and the solvent removed by rotary evaporation.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with water
  3. dry with materialdried over sodium sulfate
  4. customthe solvent removed by rotary evaporation

Sources & evidence

ORD record
ord-f60320e68df245c2be67c6a5ca450c03
Source dataset
uspto-grants-2012_07
Patent number
US08216550B2

Reaction notes

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