Hydrochloric Acid → HCID 14512529, compound

HRID 1423935Notes

Reaction equation

HRID 1423935 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[OH:11].[CH3:13][N:14]([CH3:18])[C:15](Cl)=[S:16].C1N2CCN(CC2)C1.Cl>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[O:11][C:15](=[S:16])[N:14]([CH3:18])[CH3:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9237DabcoHCID 27871Dimethylthiocarbamoyl chlorideHCID 77683Methyl 5-bromosalicylate

Product 1

HCID 14512529HCID 14512529, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-Bromo-2-hydroxy-benzoic acid methyl ester (29.8 g, 129 mmol) and dimethylthiocarbamoyl chloride (17.54 g, 142 mmol) in DMF at room temperature was added DABCO (21.7 g, 193.5 mmol). The resulting mixture, after being stirred at room temperature overnight, was diluted with water (1.25 L) and acidified to a pH˜4 using 1 N HCl. The precipitate was collected, rinsed with water and dried in vacuo to provide crude 5-bromo-2-dimethylthiocarbamoyloxy-benzoic acid methyl ester as an off-white solid in 91% yield. The product was used directly in the subsequent reaction without purification.

Workup

  1. customThe precipitate was collected
  2. washrinsed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-ce1a4dbdae5b4549b55ad9a865b6600b
Source dataset
uspto-grants-2015_01
Patent number
US08927591B2

Reaction notes

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