Hydrochloric Acid → HCID 21864958, compound

HRID 131179Notes

Reaction equation

HRID 131179 reaction equation
[C:1]([C:3]1[C:4]([S:13]C(=O)N(C)C)=[CH:5][C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1)#[N:2].C[O-].[Na+].CO.Cl>CN(C)C=O>[SH:13][C:4]1[C:3]([C:1]#[N:2])=[CH:12][C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10942334Sodium MethoxideHCID 58759672HCID 58759672, compound

Product 1

HCID 21864958HCID 21864958, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of dimethylthiocarbamic acid S-(3-cyano-5,6,7,8-tetrahydronaphthalen-2-yl) ester (1.00 g, 3.84 mmol) in anhydrous N,N-dimethylformamide (10 mL) under argon was added dropwise 25% sodium methoxide in methanol (2.6 mL, 11.5 mmol, 3.0 eq) at 0° C. The resultant yellow reaction mixture was stirred at room temperature for 1 h. The reaction mixture was poured into cold 2N HCl (100 mL) and then extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate and evaporated at reduced pressure to give 700 mg (96%) of crude 3-mercapto-5,6,7,8-tetrahydronaphthalene-2-carbonitrile.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-e6f0dc06cca24de5b783612978190c3c
Source dataset
uspto-grants-2008_06
Patent number
US07384947B2

Reaction notes

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