Hydrochloric Acid → HCID 86653094, compound

HRID 447708Notes

Reaction equation

HRID 447708 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12](=[S:14])=[S:13].[CH3:15]CN(CC)CC.IC.Cl>O1CCOCC1>[CH3:11][C:8]1[CH:9]=[CH:10][C:2]([NH:1][C:12]([S:14][CH3:15])=[S:13])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 762552-Amino-5-methylbenzoic acid

Product 1

HCID 86653094HCID 86653094, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 2-amino-5-methylbenzoic acid (2.52 g, 16.7 mmol) and carbon disulfide (2.01 mL, 33.9 mmol) in 45 mL of dry 1,4-dioxane was added NEt3 (5.58 mL, 40.0 mmol) and the mixture were stirred under N2 atmosphere at 5° C. for 18 hours. Iodomethane (1.14 mL, 18.4 mmol) was added dropwise and the mixture was stirred as 5° C. for 1 hour. The reaction was poured into 25 mL of an aqueous solution of HCl (1M) and the mixture was concentrated to half its volume under reduced pressure and extracted three times with 75 mL of EtOAc. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The residue was recrystallized from chloroform to give 3 as a yellow solid (3.25 g, 81%). mp: 199° C.

Workup

  1. stirringthe mixture was stirred as 5° C. for 1 hour
  2. concentrationthe mixture was concentrated to half its volume under reduced pressure
  3. extractionextracted three times with 75 mL of EtOAc
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from chloroform

Sources & evidence

ORD record
ord-41835483135549fca31453dc1f4b9713
Source dataset
uspto-grants-2013_07
Patent number
US08481561B2

Reaction notes

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