Ammonia → HCID 14391988, compound

HRID 1587922Notes

Reaction equation

HRID 1587922 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[S:4][CH:5]=[C:6]([C:8](=[O:11])[CH2:9]Br)[N:7]=1.O[CH2:15][CH2:16][NH:17][CH:18]([CH3:32])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:22][CH:21]=1.C([SiH](CC)CC)C.N>>[C:28]([CH2:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][CH:18]([N:17]2[CH2:16][CH2:15][O:11][CH:8]([C:6]3[N:7]=[C:3]([C:2]([F:13])([F:12])[F:1])[S:4][CH:5]=3)[CH2:9]2)[CH3:32])=[CH:21][CH:22]=1)([O:30][CH3:31])=[O:29]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 12052TriethylsilaneHCID 10978660HCID 10978660, compoundHCID 14347764HCID 14347764, compound

Product 1

HCID 14391988HCID 14391988, compound

Procedure

Prepared analogously to Example 3 by reaction of 11.6 g (0.043 mol) of 2-trifluoromethyl-4-bromoacetyl-thiazole with 23 g (0.086 mol) of N-(2-hydroxyethyl)-2-(4-carbomethoxymethoxyphenyl)-1-methylethylamine. To complete the reaction the mixture is heated to boiling for 6 hours. It is then concentrated in vacuo, and the resulting residue is dissolved in 85 ml of trifluoroacetic acid and, at room temperature, 7 g (0.06 mol) of triethylsilane are added. After 90 hours the solution is poured onto ice, and concentrated ammonia is added, and the mixture is extracted several times with methylene chloride. The organic phase is dried over sodium sulphate and concentrated, and the residue is purified on a silica gel column using toluene/ethyl acetate=8/2 as eluant.

Workup

  1. customthe reaction the mixture
  2. temperatureis heated
  3. concentrationIt is then concentrated in vacuo
  4. dissolutionthe resulting residue is dissolved in 85 ml of trifluoroacetic acid and, at room temperature
  5. additionis added
  6. extractionthe mixture is extracted several times with methylene chloride
  7. dry with materialThe organic phase is dried over sodium sulphate
  8. concentrationconcentrated
  9. customthe residue is purified on a silica gel column

Sources & evidence

ORD record
ord-e94503ecf7a44614a5384e7e65fecb96
Source dataset
uspto-grants-1993_06
Patent number
US05219852

Reaction notes

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