Triethylamine → HCID 15034423, compound

HRID 1073856Notes

Reaction equation

HRID 1073856 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:15][CH3:16])=[C:9]([S:11]([NH2:14])(=[O:13])=[O:12])[CH:10]=1.C(N(CC)CC)C.[F:24][C:25]1[CH:26]=[CH:27][C:28]([O:35][CH3:36])=[C:29]([CH:34]=1)[O:30][CH2:31][CH:32]=O.[BH4-].[Na+]>CO>[F:24][C:25]1[CH:26]=[CH:27][C:28]([O:35][CH3:36])=[C:29]([CH:34]=1)[O:30][CH2:31][CH2:32][NH:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:15][CH3:16])=[C:9]([S:11]([NH2:14])(=[O:13])=[O:12])[CH:10]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 15034422HCID 15034422, compoundHCID 21848695125960-58-9

Product 1

HCID 15034423HCID 15034423, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

A suspension of 1.50 g of 5-(2-aminoethyl)-2-methoxybenzenesulfonamide hydrochloride and 0.8 ml of triethylamine in 50 ml of methanol was heated for 30 minutes at 75° C. To the reaction mixture was added 1.00 g of 2-(5-fluoro-2-methoxyphenoxy)acetaldehyde and the reaction mixture was heated for 10 minutes at 75° C. To the solution was added 0.45 g of sodium borohydride under ice cooling and the solution was stirred for 1 hr at room temperature. The reaction mixture was evaporated, acidified with 10% hydrochloric acid and washed with ether. The aqueous layer was made alkaline with potassium carbonate and extracted with ethyl acetate. The extract was washed with water, dried and evaporated. The residue was solidified with a mixture of methanol and ether and the precipitate was filtered to give 0.46 g of the desired compound as pale brown crystals which were recrystallized from N,N-dimethylformamide as pale yellow crystals, m.p. 201°-205° C.

Workup

  1. temperaturethe reaction mixture was heated for 10 minutes at 75° C
  2. customThe reaction mixture was evaporated
  3. washwashed with ether
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. customevaporated
  8. additionThe residue was solidified with a mixture of methanol and ether
  9. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-18aad0eab7504438af6cdc000caedfac
Source dataset
uspto-grants-1990_11
Patent number
US04971990

Reaction notes

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