Acetic Acid → HCID 20785954, compound

HRID 736478Notes

Reaction equation

HRID 736478 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:13]([C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClC(Cl)C.C1COCC1>[CH3:22][O:21][C:19](=[O:20])[C:18]1[CH:23]=[CH:24][C:15]([CH2:13][NH:1][C:2]2[S:3][C:4]3[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=3[N:6]=2)=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 15294Methyl 4-FormylbenzoateHCID 156302-Amino-6-methoxybenzothiazoleHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 20785954HCID 20785954, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-6-methoxybenzothiazole (2.00 g, 11.1 mmol) in a mixture of dichloroethane (20 mL) and THF (20 mL), were successively added methyl 4-formylbenzoate (1.82 g, 11.1 mmol), sodium triacetoxyborohydride (3.53 g, 16.7 mmol) and acetic acid (1.27 mL, 22.2 mmol). The mixture was stirred over 2 days and was quenched by adding aqueous saturated solution of NaHCO3. The mixture was poured in a separating funnel containing water and was extracted with dichloromethane. The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography using EtOAc/hexane (20:80 to 30:70) to afford the title compound 232 (1.85 g, 51% yield). 1H NMR: (Acetone-d6) δ (ppm): 8.04 (d, J=8.5 Hz, 2H), 7.65 (d, J=8.8 Hz, 2H), 7.41 (d, J=8.8 Hz, 1H), 7.34 (d, J=2.5 Hz, 1H), 6.94 (dd, J=8.5, 2.7 Hz, 1H), 4.50 (t, J=5.5 Hz, 2H), 3.86 (s, 3H).

Workup

  1. customwas quenched
  2. additionby adding aqueous saturated solution of NaHCO3
  3. additionThe mixture was poured in a separating funnel
  4. additioncontaining water
  5. extractionwas extracted with dichloromethane
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-f5236554b9c6458ba40c4cffa5204b16
Source dataset
uspto-grants-2009_09
Patent number
US07595343B2

Reaction notes

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