Carbon Disulfide → HCID 178524178, compound

HRID 2224944Notes

Reaction equation

HRID 2224944 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH2:11])[C:5]([OH:7])=[O:6].[C:12](=S)=[S:13].[OH-].[K+]>O.C(O)C>[SH:13][C:12]1[NH:11][C:10]2[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=2[N:1]=1

Participants

6

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 692633,4-Diaminobenzoic acid

Product 1

HCID 178524178HCID 178524178, compoundYield 59.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3,4-diaminobenzoic acid (1.52 g, 10 mmol), carbon disulfide (0.837 g, 11 mmol), and potassium hydroxide (0.617 g, 11 mmol) in water (30 mL) and ethanol (8 mL) was heated under reflux for 16 h and then cooled to rt. The reaction mixture was evaporated in vacuo and then taken up in water (25 mL). The resulting mixture was neutralized by the addition of 1 N HCl and the resulting brown solid isolated by vacuum filtration, washed with water and air dried to provide the title compound (1.15 g, 59% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 7.20 (d, J=8.09 Hz, 1 H) 7.66 (s, 1 H) 7.76 (dd, J=8.46, 1.47 Hz, 1 H) 12.76 (s, 1 H) 12.82 (s, 1 H). MS (ESI−) m/z 193.0 (M−H)−.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 h
  3. customThe reaction mixture was evaporated in vacuo
  4. additionThe resulting mixture was neutralized by the addition of 1 N HCl
  5. customthe resulting brown solid isolated by vacuum filtration
  6. washwashed with water and air
  7. customdried

Sources & evidence

ORD record
ord-badc1cd7179d49409836a0ac25e6c6ac
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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