Triethylamine → HCID 20552957, compound

HRID 1446820Notes

Reaction equation

HRID 1446820 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].ClOC(C)(C)C.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([S:30][CH2:31][C:32]([NH2:34])=[O:33])=[CH:26][CH:25]=1.C(N(CC)CC)C>C(Cl)Cl.O1CCCC1>[NH2:1][C:2]1[C:3]([C:4](=[O:5])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[CH:12][C:13]([Cl:16])=[CH:14][C:15]=1[CH:31]([S:30][C:27]1[CH:28]=[CH:29][C:24]([Cl:23])=[CH:25][CH:26]=1)[C:32]([NH2:34])=[O:33]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 128702-Amino-5-chlorobenzophenoneHCID 2422672-[(4-chlorophenyl)sulfanyl]acetamideHCID 521297Tert-Butyl hypochlorite

Product 1

HCID 20552957HCID 20552957, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (-70° C.) solution of 20 g (0.0863 mole) of 2-amino-5-chlorobenzophenone in 500 ml of methylene chloride under nitrogen atmosphere was added a solution of 9.48 g (0.088 mole) of t-butyl hypochlorite in 50 ml of methylene chloride. After an additional 15 min stirring, a solution of 17.35 g (0.0863 mole) of α-(4-chlorophenylthio)acetamide in 500 ml of a 50/50 mixture of tetrahydrofuran and methylene chloride was added. The mixture was stirred at -70° C. for 2 hr, 8.72 g (0.0863 mole) of triethylamine was added, and the stirred solution was allowed to warm to room temperature over a period of 2 hr. The reaction mixture was extracted with several portions of water and the organic layer dried over magensium sulfate. The volume of liquid was reduced to about 500 ml. Methylene chloride, 500 ml, was added to precipitate the product which after filtration and drying weighed 16.62 g (44.7%). The yellow solid melted at 198°-200° C.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at -70° C. for 2 hr
  3. extractionThe reaction mixture was extracted with several portions of water
  4. dry with materialthe organic layer dried over magensium sulfate
  5. additionMethylene chloride, 500 ml, was added
  6. customto precipitate the product which
  7. filtrationafter filtration
  8. customdrying

Sources & evidence

ORD record
ord-4983969e331c4cf0891e622fe0528b16
Source dataset
uspto-grants-1982_02
Patent number
US04313949

Reaction notes

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