Triethylamine → HCID 20552958, compound

HRID 1446822Notes

Reaction equation

HRID 1446822 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[CH3:16][S:17][CH2:18][C:19]([NH:21][CH3:22])=[O:20].C(OCl)(C)(C)C.C(N(CC)CC)C>C(Cl)Cl>[NH2:1][C:2]1[C:3]([C:4](=[O:5])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[CH:12][CH:13]=[CH:14][C:15]=1[CH:18]([S:17][CH3:16])[C:19]([NH:21][CH3:22])=[O:20]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 760802-AminobenzophenoneHCID 521297Tert-Butyl hypochloriteHCID 13553138HCID 13553138, compound

Product 1

HCID 20552958HCID 20552958, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 29.6 g (0.15 mole) of 2-aminobenzophenone in 350 ml of methylene chloride was cooled to -70° C. and 17.9 g (0.15 mol) of 2-methylthio-N-methylacetamide in 20 ml of methylene chloride was added. To the (-70° C.) mixture was added dropwise a solution of 17.2 g (0.15 mole) of 95% t-butylhypochlorite in 30 ml of methylene chloride. The temperature was maintained at or below -65° C. for 1.5 hr, then 15.1 g (0.15 mole) of triethylamine was added rapidly. The solution was allowed to warm to room temperature and was washed with water. The organic solution was concentrated and the residue crystallized when mixed with isopropyl ether. The solid was recrystallized from isopropyl alcohol to give 31 g (65%) of yellow needles, m.p. 149.0°-150.0° C.

Workup

  1. temperatureThe temperature was maintained at or below -65° C. for 1.5 hr
  2. washwas washed with water
  3. concentrationThe organic solution was concentrated
  4. customthe residue crystallized when
  5. additionmixed with isopropyl ether
  6. customThe solid was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-f43d5de94eaf463ebbd72af5054460ef
Source dataset
uspto-grants-1982_02
Patent number
US04313949

Reaction notes

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