Hydrochloric Acid → (E)-methyl 2-[2-(3-chlorosulphonylphenoxy)phenyl]-3-methoxypropenoate

HRID 1741880Notes

Reaction equation

HRID 1741880 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1/[C:12](=[CH:17]\[O:18][CH3:19])/[C:13]([O:15][CH3:16])=[O:14].[ClH:23].N([O-])=O.[Na+].[S:28](=[O:30])=[O:29]>C(O)(=O)C.O>[Cl:23][S:28]([C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1/[C:12](=[CH:17]\[O:18][CH3:19])/[C:13]([O:15][CH3:16])=[O:14])(=[O:30])=[O:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 15125769(E)-methyl 2-[2-(3-aminophenoxy)phenyl]-3-methoxypropenoateHCID 23668193Sodium Nitrite

Product 1

HCID 15125770(E)-methyl 2-[2-(3-chlorosulphonylphenoxy)phenyl]-3-methoxypropenoate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

A solution of (E)-methyl 2-[2-(3-aminophenoxy)-phenyl]-3-methoxypropenoate (0.4 g) in glacial acetic acid (2 ml) was treated with 5.8M hydrochloric acid (1 ml), at -10° C. The stirred solution was then treated with sodium nitrite (0.1 g in 2 ml of water) still at -10° C. After 30 minutes, the resulting solution (containing the diazonium salt) was added to a stirred mixture of glacial acetic acid (0.5 ml) saturated with sulphur dioxide, containing 0.1 g of cuprous chloride (effervescence). After 30 minutes, the reaction mixture was poured into water and extracted with ether. The ether extracts were neutralized with a saturated aqueous solution of sodium bicarbonate, dried and concentrated to give (E)-methyl 2-[2-(3-chlorosulphonylphenoxy)phenyl ]-3-methoxypropenoate (0.14 g) as a yellow oil.

Workup

  1. waitAfter 30 minutes
  2. extractionextracted with ether
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-05723ebc459d4384abee68b71ebdac3c
Source dataset
uspto-grants-1994_08
Patent number
US05334748

Reaction notes

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