Acetic Acid → 2-Chloro-6-isopropylaminobenzothiazole

HRID 604231Notes

Reaction equation

HRID 604231 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 μl), 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-23c1abf390504c869f567d9963307c7c
Source dataset
uspto-grants-2011_03
Patent number
US07910087B2

Reaction notes

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