Water → HCID 13937614, compound

HRID 648850Notes

Reaction equation

HRID 648850 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:6]=1[CH2:14][S:15](Cl)(=[O:17])=[O:16])=[O:4].[OH-].[NH4+:20].O>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:6]=1[CH2:14][S:15]([NH2:20])(=[O:17])=[O:16])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 13937613HCID 13937613, compound

Product 1

HCID 13937614HCID 13937614, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude product from Example 3 (15.1 g) was dissolved in 150 ml tetrahydrofuran and this solution was contacted at 0° C. with concentrated aqueous ammonium hydroxide. The resulting suspension was allowed to warm to room temperature over a 15-minute period and the solvent was removed in vacuo to yield an oily solid. Addition of water to this crude material resulted in gradual crystallization. The aqueous layer was extracted with ethyl acetate and the combined extracts were dried and concentrated in vacuo to give a yellow oil which solidified upon scratching. This material was washed with warm n-butyl chloride, filtered and dried to give the title compound as a pale yellow solid, m.p. 119°-123°; IR(nujol): 3490, 3330, 1710 cm-1 ; NMR (CDCl3): δ 4.0 (3H, s, CO2CH3), 5.4 (2H, s, --CH2 --), 6.8 (2H, s, NH2), 7.5-8.25 (3H, m).

Workup

  1. customthe solvent was removed in vacuo
  2. customto yield an oily solid
  3. customresulted in gradual crystallization
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. customthe combined extracts were dried
  6. concentrationconcentrated in vacuo
  7. customto give a yellow oil which
  8. washThis material was washed with warm n-butyl chloride
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-2819e8367f0b4caca3983f18fe294179
Source dataset
uspto-grants-1988_04
Patent number
US04737185

Reaction notes

Loading…