Acetic Acid → 2-Chloro-6-isopropylaminobenzothiazole

HRID 1511492Notes

Reaction equation

HRID 1511492 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.[CH3:12][C:13]([CH3:15])=O.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][CH:13]([CH3:15])[CH3:12])[CH:11]=[CH:10][C:5]=2[N:6]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 109212032-Chloro-1,3-benzothiazol-6-amine

Product 1

HCID 670406982-Chloro-6-isopropylaminobenzothiazole

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 acetone (14.5 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-f7bcb83d2d25444d826ed6afdb55f3e7
Source dataset
uspto-grants-2012_07
Patent number
US08216550B2

Reaction notes

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