Hydrochloric Acid → HCID 20550950, compound

HRID 1447422Notes

Reaction equation

HRID 1447422 reaction equation
[CH3:1][CH:2]([N:11]=[C:12]([CH3:23])[C:13]([C:15]1[S:19][CH:18]=[C:17]([C:20]([NH2:22])=[O:21])[CH:16]=1)=[O:14])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[BH4-].[Na+].[ClH:26].C(=O)(O)[O-].[Na+]>CO.C(OCC)(=O)C>[ClH:26].[OH:14][CH:13]([C:15]1[S:19][CH:18]=[C:17]([C:20]([NH2:22])=[O:21])[CH:16]=1)[CH:12]([NH:11][CH:2]([CH3:1])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:23]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 20550955HCID 20550955, compound

Product 1

HCID 20550950HCID 20550950, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

An ice-cold solution of 5-[2-[(1-methyl-3-phenylpropyl)imino]-1-oxopropyl]thiophene-3-carboxamide (0.7 g) in methanol (50 ml) was treated portionwise with sodium borohydride (0.76 g), stirred at 0° for 1 h, poured onto ice, acidified with dilute hydrochloric acid (2 N), neutralised with aqueous sodium bicarbonate (8%), and extracted with ethyl acetate (2×300 ml). The extract was washed with brine (50 ml) and evaporated to a small volume (ca. 20 ml) to deposit a fine white solid (0.47 g) which was partitioned between ethyl acetate (2×300 ml) and aqueous sodium bicarbonate (1 M; 100 ml). The organic solution (MgSO4) was dried and evaporated to give an off-white foam which was dissolved in ethyl acetate (ca. 100 ml) and treated with ethereal hydrogen chloride to precipitate the title compound (0.42 g) m.p. 125°-130°. TLC SiO2 (3% Et3N/20% i-PrOH/EtOAc) Rf 0.22 and 0.27.

Workup

  1. additionpoured onto ice
  2. extractionextracted with ethyl acetate (2×300 ml)
  3. washThe extract was washed with brine (50 ml)
  4. customevaporated to a small volume (ca. 20 ml)
  5. customwas partitioned between ethyl acetate (2×300 ml) and aqueous sodium bicarbonate (1 M; 100 ml)
  6. dry with materialThe organic solution (MgSO4) was dried
  7. customevaporated
  8. customto give an off-white foam which
  9. customto precipitate the title compound (0.42 g) m.p. 125°-130°

Sources & evidence

ORD record
ord-9f54a22a469b493bb766ef2dbccbb164
Source dataset
uspto-grants-1982_02
Patent number
US04316907

Reaction notes

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