Carbon Disulfide → HCID 178524257, compound

HRID 1736336Notes

Reaction equation

HRID 1736336 reaction equation
Cl[C:2]1[C:10]([N+:11]([O-])=O)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].[S].[C:27](=[S:29])=[S:28]>[OH-].[Na+].O.C(O)(=O)C>[C:4]([C:3]1[C:2]2[S:28][C:27]([SH:29])=[N:11][C:10]=2[CH:9]=[CH:8][CH:7]=1)([OH:6])=[O:5]

Participants

8

Reactant 4

HCID 6348Carbon DisulfideHCID 198702-Chloro-3-nitrobenzoic acidHCID 73972Sodium sulfide nonahydrateHCID 5362487Sulfur

Product 1

HCID 178524257HCID 178524257, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
45 °C

Procedure

2-Chloro-3-nitrobenzoic acid (8.06 g, 0.04 mol) in 1N sodium hydroxide (50 mL) was added to a polysulfide solution made from sodium sulfide nonahydrate (28.82 g, 0.12 mol) and sulfur (9.60 g, 0.30 mol) in water (30 mL). The resulting mixture was stirred and heated at reflux for 5.5 hours. The reaction mixture was cooled to 45° C., treated with carbon disulfide (4.81 mL, 0.08 mL), and stirred at 45° C. for 20 hours. The mixture was cooled in an ice bath and neutralized by slowly adding acetic acid (7 g). The solid precipitate was collected, washed with ice-cold water, suspended in saturated sodium carbonate solution (100 mL), and filtered to remove insolubles. The filtrate was acidified with acetic acid (33 g) and filtered to collect the insoluble material. The filter cake was dried under vacuum to afford crude 7-carboxy-2-mercaptobenzothiazole (0.70 g) as a brownish gray solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5.5 hours
  3. stirringstirred at 45° C. for 20 hours
  4. temperatureThe mixture was cooled in an ice bath
  5. customThe solid precipitate was collected
  6. washwashed with ice-cold water
  7. filtrationfiltered
  8. customto remove insolubles
  9. filtrationfiltered
  10. customto collect the insoluble material
  11. customThe filter cake was dried under vacuum

Sources & evidence

ORD record
ord-b6db020797fe47b38d60bf52ee90dc8d
Source dataset
uspto-grants-1996_07
Patent number
US05541176

Reaction notes

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