Hydrochloric Acid → HCID 59750383, compound

HRID 1746183Notes

Reaction equation

HRID 1746183 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[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]=[CH:8][C:7]([Br:10])=[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 13983552Methyl 4-bromo-2-hydroxybenzoate

Product 1

HCID 59750383HCID 59750383, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-bromo-2-hydroxy-benzoic acid methyl ester (Mori, N. et al, Bull Chem. Soc. Jpn. 1969, 42(2), 488-491) (29.3 g, 127 mmol) and dimethylthiocarbamoyl chloride (17.2 g, 140 mmol) in DMF at room temperature was added DABCO (21.3 g, 190 mmol). The resulting mixture, after being stirred at room temperature overnight, was diluted with water (1.25 L) and acidified to a pH of around 4 using 1 N HCl. The precipitate was collected, rinsed with water and dried in vacuo to provide 4-bromo-2-dimethylthiocarbamoyloxy-benzoic acid methyl ester as an off-white solid (36.8 g). 1H NMR (200 MHz, CDCl3): δ (ppm)=7.84 (d, J=8.2 Hz, 1H), 7.43 (dd, J=8.6, 2.0 Hz, 1H), 7.29 (d, J=2.0 Hz, 1H), 3.83 (s, 3H), 3.45 (s, 3H), 3.38 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-3ecf2f5fddbf44338bc9bb7de3653e56
Source dataset
uspto-grants-2015_10
Patent number
US09149476B2

Reaction notes

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