Methanol → HCID 11384290, compound

HRID 2172202Notes

Reaction equation

HRID 2172202 reaction equation
CO.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[N:17]1([C:23]2[S:24][C:25]3[CH:31]=[C:30]([OH:32])[CH:29]=[CH:28][C:26]=3[N:27]=2)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.[F:33][C:34]([F:45])([F:44])[O:35][C:36]1[CH:43]=[CH:42][C:39]([CH:40]=O)=[CH:38][CH:37]=1>O.ClCCCl.C(O)(=O)C>[F:33][C:34]([F:44])([F:45])[O:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40][N:20]2[CH2:19][CH2:18][N:17]([C:23]3[S:24][C:25]4[CH:31]=[C:30]([OH:32])[CH:29]=[CH:28][C:26]=4[N:27]=3)[CH2:22][CH2:21]2)=[CH:38][CH:37]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 69573p-(Trifluoromethoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 70873578HCID 70873578, compound

Product 1

HCID 11384290HCID 11384290, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Methanol (1 ml) and a catalytic amount of acetic acid and sodium triacetoxyborohydride (0.14 g) were added to a 1,2-dichloroethane solution (5 ml) of 2-piperazin-1-yl-benzothiazol-6-ol (0.1 g) and 4-trifluoromethoxybenzaldehyde (0.067 ml) and stirred at room temperature overnight. Water was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was washed with water, dried over sodium sulfate, and then concentrated under reduced pressure to afford the title compound as a colorless amorphous compound (80 mg).

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7359fc53098b4777b9ef1d89bc03abb5
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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