Chlorosulfonic acid → HCID 57118747, compound

HRID 1682090Notes

Reaction equation

HRID 1682090 reaction equation
[CH2:1]([N:5]1[C:12](=[O:13])[C:11]2[CH2:14][CH:15]3[CH2:17][CH:6]1[CH:7]=[CH:8][S:9][C:10]=2[S:16]3)[CH:2]([CH3:4])[CH3:3].COC1C=CC(C[NH2:25])=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl.Cl[S:35]([OH:38])(=O)=[O:36]>>[CH2:1]([N:5]1[C:12](=[O:13])[C:11]2[CH2:14][CH:15]3[CH2:17][CH:6]1[CH:7]=[C:8]([S:35]([NH2:25])(=[O:38])=[O:36])[S:9][C:10]=2[S:16]3)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 4

HCID 24638Chlorosulfonic acidHCID 24819Phosphorus pentachlorideHCID 754524-MethoxybenzylamineHCID 67848967HCID 67848967, compound

Product 1

HCID 57118747HCID 57118747, compound

Procedure

5-Isobutyl-4-oxo-3,4,5,6-tetrahydro-2H-2,6-methanothieno[3,2-g]-1,5-thiazocine, prepared as described in Example 2, steps A and B but substituting isobutylamine for 4-methoxybenzylamine (4 g, 15 mmol), was added to a mixture of phosphorous pentachloride (6.23 g, 30 mmol) and chlorosulfonic acid (7 ml) at 0° C. After 0.5 hour at this temperature and 0.5 hour at 50° C., the reaction mixture was poured over crushed ice. The resulting sulfonyl chloride was separated and treated with concentrated aqueous ammonia (100 ml) in ethyl acetate (100 ml) at 0° C. The ethyl acetate layer was separated and evaporated under reduced pressure. The resulting solid was chromatographed over silica gel (ethyl acetate: hexane; 1:1) to give 2.0 g of the title compound.

Workup

  1. additionthe reaction mixture was poured
  2. customover crushed ice
  3. customThe resulting sulfonyl chloride was separated
  4. additiontreated with concentrated aqueous ammonia (100 ml) in ethyl acetate (100 ml) at 0° C
  5. customThe ethyl acetate layer was separated
  6. customevaporated under reduced pressure
  7. customThe resulting solid was chromatographed over silica gel (ethyl acetate: hexane; 1:1)

Sources & evidence

ORD record
ord-d6281292abd84a0ca4d13f84ad927c09
Source dataset
uspto-grants-1992_12
Patent number
US05175284

Reaction notes

Loading…