Triethylamine → 2-Amino-3-(4-fluorobenzoyl)-alpha-(n-propylthio)-phenylacetamide

HRID 2259720Notes

Reaction equation

HRID 2259720 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH2:15])=[CH:4][CH:3]=1.[C:17]([O:21]Cl)(C)(C)[CH3:18].[CH2:23]([CH2:26][C:27](N)=[S:28])CC.C([N:32](CC)CC)C>C(Cl)Cl>[NH2:15][C:10]1[C:9]([C:8](=[O:16])[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:14][CH:13]=[CH:12][C:11]=1[CH:18]([S:28][CH2:27][CH2:26][CH3:23])[C:17]([NH2:32])=[O:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 521297Tert-Butyl hypochloriteHCID 98372872-Amino-4'-fluorobenzophenoneHCID 12534254Pentanethioamide

Product 1

HCID 153436062-Amino-3-(4-fluorobenzoyl)-alpha-(n-propylthio)-phenylacetamideYield 56.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 21.5 g (0.1 mole) of 4'-fluoro-2-aminobenzophenone in 400 mL of methylene chloride was cooled to -70° C. and 11.5 g (0.1 mole) of 95% t-butylhypochlorite was added over a period of 15 min, keeping the temperature below -66° C. To this solution was added a solution of 13.3 g of 2-n-propylthioacetamide in 50 mL of methylene chloride over a 10 min period. The solution was stirred for 1 h at -65° to -70° C. and then allowed to warm to 0° C. at which point 10.2 g (0.1 mole) of triethylamine was added. The solution was stirred for 10 min and then washed with water. The organic solution was dried over magnesium sulfate. After concentrating under reduced pressure, the residue was crystallized from isopropyl alcohol and dried to give 19.5 g (56%) of yellow crystals melting at 140°-142° C.

Workup

  1. customthe temperature below -66° C
  2. additionwas added
  3. stirringThe solution was stirred for 10 min
  4. washwashed with water
  5. dry with materialThe organic solution was dried over magnesium sulfate
  6. concentrationAfter concentrating under reduced pressure
  7. customthe residue was crystallized from isopropyl alcohol
  8. customdried

Sources & evidence

ORD record
ord-eb59087061c74d43906cb1e9077ddb40
Source dataset
uspto-grants-1995_12
Patent number
US05475034

Reaction notes

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