Hydrochloric Acid → 4-Dimethylthiocarbamoyloxy-7-phenoxy-isoquinoline-3-carboxylic acid butyl ester

HRID 2060412Notes

Reaction equation

HRID 2060412 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].[CH3:26][N:27]([CH3:31])[C:28](Cl)=[S:29].N12CCN(CC1)CC2.Cl>CN(C=O)C>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:17]=1[O:18][C:28](=[S:29])[N:27]([CH3:31])[CH3:26])=[CH:15][CH:14]=[C:13]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9237DabcoHCID 27871Dimethylthiocarbamoyl chlorideHCID 667129514-Hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid butyl ester

Product 1

HCID 865954644-Dimethylthiocarbamoyloxy-7-phenoxy-isoquinoline-3-carboxylic acid butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.5 g of 4-Hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid butyl ester, Example A-65.f, in 6.3 ml of anhydrous DMF was added 578 mg of dimethylthiocarbamoylchloride and 1.5 g of 1,4-diazabicyclo[2.2.2]octane. The mixture was stirred overnight at room temperature. The mixture was poured into 30 ml of 1 N HCl and extracted three times with 30 ml portions of ethyl acetate. The organic fractions were washed with water and brine, dried over anhydrous sodium sulfate, and concentrated to 1.9 g of product; MS (+) m/z 425.27 (M+1)

Workup

  1. extractionextracted three times with 30 ml portions of ethyl acetate
  2. washThe organic fractions were washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated to 1.9 g of product

Sources & evidence

ORD record
ord-a755f079ec0d4d0ebfa8d7ff781647a9
Source dataset
uspto-grants-2012_10
Patent number
US08278325B2

Reaction notes

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