Triethylamine → HCID 13394282, compound

HRID 2164296Notes

Reaction equation

HRID 2164296 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)=[O:5].CC[C:19](OCC)=[S:20].[C:24]([O:28]Cl)(C)(C)[CH3:25].C(N(CC)CC)C>C(Cl)Cl>[F:12][C:9]1[CH:10]=[CH:11][C:6]([C:4]([C:3]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:2]=2[NH:1][C:24](=[O:28])[CH:25]3[S:20][CH3:19])=[O:5])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 521297Tert-Butyl hypochloriteHCID 98372872-Amino-4'-fluorobenzophenoneHCID 12284386Ethyl methylthioacetate

Product 1

HCID 13394282HCID 13394282, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 42.2 g (0.196 mole) of 2-amino-4'-fluorobenzophenone in 2 liters of methylene chloride was cooled to -65° C. and 26.5 g (0.198 mole) of ethyl methylthioacetate was added. A solution of 23.0 g (0.21 mole) of 95% tertiary butoxychloride in 50 ml of methylene chloride was added dropwise, keeping the temperature below -65° C. One hour after the addition was complete, 22.2 g (0.22 mol) of triethylamine was added dropwise and the mixture was allowed to warm to room temperature. The solution was concentrated to 700 ml and then washed with water. The organic solution was concentrated and the residue dissolved in 400 ml of methanol containing 30 ml of concentrated hydrochloric acid. The mixture was heated at reflux for one hour followed by cooling. The mixture was allowed to stand overnight, the crystals collected and washed with methanol to yield 31.4 g (53%) as bright yellow solid, m.p. 165°- 167.5° C.

Workup

  1. customthe temperature below -65° C
  2. additionOne hour after the addition
  3. concentrationThe solution was concentrated to 700 ml
  4. washwashed with water
  5. concentrationThe organic solution was concentrated
  6. dissolutionthe residue dissolved in 400 ml of methanol containing 30 ml of concentrated hydrochloric acid
  7. temperatureThe mixture was heated
  8. temperatureat reflux for one hour
  9. temperatureby cooling
  10. customthe crystals collected
  11. washwashed with methanol
  12. customto yield 31.4 g (53%) as bright yellow solid, m.p. 165°- 167.5° C.

Sources & evidence

ORD record
ord-71b3455e819a40bd830507e992e5e4c6
Source dataset
uspto-grants-1985_03
Patent number
US04503073

Reaction notes

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