Acetic Acid → 2-Chloro-6-butylaminobenzothiazole

HRID 604233Notes

Reaction equation

HRID 604233 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)[CH2:13][CH2:14][CH3:15].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][CH2:13][CH2:14][CH3:15])[CH:11]=[CH:10][C:5]=2[N:6]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 261ButanalHCID 5049666Sodium triacetoxyborohydrideHCID 109212032-Chloro-1,3-benzothiazol-6-amine

Product 1

HCID 670401982-Chloro-6-butylaminobenzothiazoleYield 91.8%

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 butyraldehyde (18 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, yielding 44.2 mg of a yellow solid. 1H-NMR (CDCl3): δ 7.67 (d, 1H, J=9.2 Hz), 6.84 (d, 1H, 3=2.4 Hz), 6.72 (dd, 1H, 3=2.4, 9.2 Hz), 3.35 (bt, 1H), 3.15 (t, 2H), 1.65 (m, 2H), 1.45 (m, 2H), 0.97 (t, 3H, J=7.6 Hz).

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-330f72f547b24048b9cd0708cf87fe69
Source dataset
uspto-grants-2011_03
Patent number
US07910087B2

Reaction notes

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