Triethylamine → HCID 20552973, compound

HRID 1446821Notes

Reaction equation

HRID 1446821 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.[C:23]1([S:29][CH2:30][C:31]([NH2:33])=[O:32])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=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:30]([S:29][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:31]([NH2:33])=[O:32]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 128702-Amino-5-chlorobenzophenoneHCID 3521622-phenylsulfanylacetamideHCID 521297Tert-Butyl hypochlorite

Product 1

HCID 20552973HCID 20552973, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (-70° C.) solution of 80.72 g (0.349 mole) of 2-amino-5-chlorobenzophenone in 1.5 liter of methylenechloride, under nitrogen atmosphere, was added 39.1 g (0.360 mole) of t-butyl hypochlorite in 100 ml of methylene chloride. After stirring for 10 min, a solution of 59.1 g (0.354 mole) of α-(phenylthio)acetamide in 1.5 liter of tetrahydrofuran was added. The mixture was stirred for 1.25 hr at -65° C., 37.5 g (0.371 mole) of triethylamine was added and the solution was allowed to warm to room temperature. The reaction mixture was extracted with several portions of water and the organic layer was dried over anhydrous sodium sulfate. The volume of solution was reduced in vacuo and yellow solid precipitated which when recrystallized from acetonitrile was a yellow crystalline solid, m.p. 190°-191° C.(d). Analysis: Calculated for C21H17N2O2SCl: C,63.55; H,4.32; N,7.06. Found: C,63.62 ; H,4.29; N,7.08.

Workup

  1. stirringThe mixture was stirred for 1.25 hr at -65° C.
  2. extractionThe reaction mixture was extracted with several portions of water
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. customprecipitated which when
  5. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-ad317ac81c6f44e9ac524c59ef41c0de
Source dataset
uspto-grants-1982_02
Patent number
US04313949

Reaction notes

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