Sodium Sulfate → 6-Methoxy-2-phenyl-5-hydroxymethylbenzothiazole

HRID 840607Notes

Reaction equation

C[O:2][C:3]([C:5]1[C:6]([O:20][CH3:21])=[CH:7][C:8]2[S:12][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:10][C:9]=2[CH:19]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:21][O:20][C:6]1[C:5]([CH2:3][OH:2])=[CH:19][C:9]2[N:10]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[S:12][C:8]=2[CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A 1 liter round bottom flask was charged with 12.88 grams (45.2 mmol) of methyl-6-methoxy-2-phenyl-5-benzothiazolecarboxylate (as part of a mixture of regioisomeric carboxylates) in 600 mL of dry tetrahydrofuran (THF). This solution was cooled to 0° C. and treated with 67.8 mL (67.8 mmol) of a 1.0 M solution of lithium aluminum hydride in THF. The dark reaction mixture was stirred for 5 hours under nitrogen. The reaction was worked up by the careful dropwise addition of a saturated aqueous solution of sodium sulfate until a granular precipitate formed. The suspension was filtered and evaporated. The residue was dissolved in ethyl acetate and washed with water and saturated brine solution. The organic phase was dried over sodium sulfate and evaporated. This product was used directly in the next step. (10.94 grams crude yield)

Workup

customThe dark reaction mixture
customformed
filtrationThe suspension was filtered
customevaporated
dissolutionThe residue was dissolved in ethyl acetate
washwashed with water and saturated brine solution
dry with materialThe organic phase was dried over sodium sulfate
customevaporated
custom(10.94 grams crude yield)

Sources & evidence

ORD record: ord-66b81aee6c1b4a1b8ca0ec7abacd9417
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06369074B1

Reaction notes

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