Hydrochloric Acid → HCID 178527430, compound

HRID 1282790Notes

Reaction equation

HRID 1282790 reaction equation
N[C:2]1[C:3]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:4]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[S:8].[ClH:25].N([O-])=O.[Na+].[S:30](=[O:32])=[O:31]>[Cu](Cl)Cl.C(O)(=O)C>[CH2:12]([S:11][C:4]1[CH:5]=[C:6]([CH:10]=[C:2]([S:30]([Cl:25])(=[O:32])=[O:31])[C:3]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:7]([OH:9])=[S:8])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 23668193Sodium NitriteHCID 178507797HCID 178507797, compound

Product 1

HCID 178527430HCID 178527430, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 176Acetic AcidSolvent2×

Conditions

Temperature
5 °C

Procedure

5-Amino-3-benzylthio-4-phenylthiobenzoic acid (1.1 g), acetic acid (10 ml), and concentrated hydrochloric acid (10 ml) is stirred and cooled to 5°C. At this temperature a concentrated solution of sodium nitrite (0.21 g) is added slowly while stirring. The resultng diazonium mixture is poured into acetic acid (20 ml), saturated with sulphur dioxide and containing copper chloride (0.2 g CuCl2, 2 H2O). The reaction mixture is allowed to reach room temperature while stirring. After 30 minutes, the precipitated 3-benzylthio-5-chlorosulfonyl-4-phenylthiobenzoic acid is collected, washed with aqueous acetic acid and dried in vacuo at room temperature.

Workup

  1. customto reach room temperature
  2. stirringwhile stirring
  3. customthe precipitated 3-benzylthio-5-chlorosulfonyl-4-phenylthiobenzoic acid is collected
  4. washwashed with aqueous acetic acid
  5. customdried in vacuo at room temperature

Sources & evidence

ORD record
ord-65c5e5a601d7433cb48276109c3a2bff
Source dataset
uspto-grants-1976_08
Patent number
US03972886

Reaction notes

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