Chlorosulfonic acid → HCID 57118747, compound

HRID 1741584Notes

Reaction equation

HRID 1741584 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]-l,5-thiazocine, prepared as described in Example 1, steps A, B and C 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-dd2204657da048d890b6b828f36f0c7e
Source dataset
uspto-grants-1994_08
Patent number
US05334591

Reaction notes

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