Hydrochloric Acid → HCID 86616004, compound

HRID 1987578Notes

Reaction equation

HRID 1987578 reaction equation
N[C:2]1[CH:3]=[C:4]([S:9]([OH:12])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.N([O-])=O.[Na+].[CH3:18][S:19]SC>O>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([S:9]([OH:12])(=[O:11])=[O:10])=[CH:3][C:2]=1[S:19][CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 12232Dimethyl DisulfideHCID 66817Benzenesulfonic acid, 3-amino-4-chloro-HCID 23668193Sodium Nitrite

Product 1

HCID 86616004HCID 86616004, compoundYield 291.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of 3-amino-4-chloro-benzenesulfonic acid (5.00 g, 24 mmol) in distilled water (38 mL) and concentrated HCl (6 mL, 72 mmol) at 0° C. was added sodium nitrite (1.99 g, 28.9 mmol) in H2O (10 mL). After 1.5 h, the mixture was allowed to warm to 25° C. and stirred for 1.5 h. Methyl disulfide (10.7 mL, 120 mmol) was added and the mixture heated to 70° C. for 18 h. The solvent was removed, in vacuo, to give an orange solid (16.7 g) that was used as is in the next reaction.

Workup

  1. temperaturethe mixture heated to 70° C. for 18 h
  2. customThe solvent was removed, in vacuo

Sources & evidence

ORD record
ord-54f1f3f8d62143288ddbbd602e2acee8
Source dataset
uspto-grants-2009_06
Patent number
US07550629B2

Reaction notes

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