Hydrochloric Acid → HCID 18977936, compound

HRID 2393044Notes

Reaction equation

HRID 2393044 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:9]([OH:11])=[O:10].Cl.[CH3:17][S:18]SC>O.C(O)(=O)C.[Cu]>[CH3:15][C:14]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[S:18][CH3:17]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 12232Dimethyl DisulfideHCID 755683-Amino-4-methylbenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 18977936HCID 18977936, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalyst2×HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
35 °C

Procedure

A solution of sodium nitrite (14.5 g) in water was added to a stirred, cooled suspension of 3-amino-4-methylbenzoic acid (30.23 g) in a mixture of acetic acid and concentrated hydrochloric acid at a temperature between 0° C. and 5° C. The mixture was stirred at 0°-5° C. for 1 hour and the resulting mixture was added to a stirred mixture of dimethyl disulphide (22 ml) and copper powder (0.25 g) in acetic acid while maintaining the temperature at about 35° C. Further copper powder (3 g) was added during the reaction in order to maintain the gas evolution. It was stirred for a further 1 hour then poured into water and the solid filtered off. It was treated with a mixture of ethyl acetate and cyclohexane, heated and the insoluble material was filtered off to give 4-methyl-3-methylsulphenylbenzoic acid (19.5 g) as a white solid, m.p. 174.6°-175.2° C.

Workup

  1. temperaturecooled
  2. temperatureto maintain the gas evolution
  3. stirringIt was stirred for a further 1 hour
  4. filtrationthe solid filtered off
  5. additionIt was treated with a mixture of ethyl acetate and cyclohexane
  6. temperatureheated
  7. filtrationthe insoluble material was filtered off

Sources & evidence

ORD record
ord-fd853b770db246898cc206c434fa0b44
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Reaction notes

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