Ammonium Chloride → [6-(Benzothiazol-2-yloxy)-benzo[b]thiophen-2-yl]-methanol

HRID 1947483Notes

Reaction equation

HRID 1947483 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([O:14][C:15]3[S:16][C:17]4[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=4[N:19]=3)[CH:12]=[CH:13][C:7]=2[CH:6]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-]>C(Cl)Cl>[S:16]1[C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=[C:15]1[O:14][C:11]1[CH:12]=[CH:13][C:7]2[CH:6]=[C:5]([CH2:3][OH:2])[S:9][C:8]=2[CH:10]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 68771517HCID 68771517, compound

Product 1

HCID 68768803[6-(Benzothiazol-2-yloxy)-benzo[b]thiophen-2-yl]-methanolYield 103.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution 6-(benzothiazol-2-yloxy)-benzo[b]thiophene-2-carboxylic acid methyl ester (274 mg, 0.8 mmol) in DCM (8 mL) was added LAH (2 M in THF, 0.4 mL, 0.3 g, 0.8 mmol) and the reaction mixture was stirred (0° C., 3 h). The reaction mixture was treated with saturated aqueous NH4Cl (2 mL) and partitioned with DCM (20 mL). The organic layer was separated and the aqueous layer was extracted with DCM (2×15 mL). The organic layer was dried, filtered and concentrated in vacuo to provide the title compound as a yellow solid (259 mg, 77%). MS (ESI): mass calcd. for C16H11O2S2, 313.0; m/z found, 314.0 [M+H]+.

Workup

  1. custompartitioned with DCM (20 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with DCM (2×15 mL)
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-489a61e9d2d74fee8be0f45c64486507
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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