Thionyl Chloride → HCID 20483193, compound

HRID 647763Notes

Reaction equation

HRID 647763 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][CH2:8][N:9]([CH:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][C:19]=2[O:23][CH3:24])[CH2:14]1)[CH2:10][CH2:11][CH3:12]>C(Cl)(Cl)Cl>[Cl:3][CH2:6][CH2:7][CH2:8][N:9]([CH:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][C:19]=2[O:23][CH3:24])[CH2:14]1)[CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 20483195HCID 20483195, compound

Product 1

HCID 20483193HCID 20483193, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

185.8 g thionylchloride are added to 190 g 1,2,3,4-tetrahydro-2-[N-(3-hydroxypropyl)-N-propylamino]-5-methoxy-naphthalene (free base) in 1.5 liters chloroform. The resultant warm reaction mixture is refluxed for 1 hour, and after concentration partitioned between methylene chloride and 2 N sodium hydroxide. The organic phase is washed with water, dried over sodium sulphate, filtered and concentrated. The crude heading compound so obtained is converted into the bis[base]naphthalene-1,5-disulphonate. M.pt. 239°-242° (decomp).

Workup

  1. temperatureThe resultant warm
  2. customreaction mixture
  3. temperatureis refluxed for 1 hour
  4. concentrationafter concentration
  5. custompartitioned between methylene chloride and 2 N sodium hydroxide
  6. washThe organic phase is washed with water
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customso obtained

Sources & evidence

ORD record
ord-929c68c77e294b35823111d7125f21f2
Source dataset
uspto-grants-1983_10
Patent number
US04410519

Reaction notes

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