Dimethylamine → HCID 69752111, compound

HRID 2301045Notes

Reaction equation

HRID 2301045 reaction equation
[CH3:1][NH:2][CH3:3].[Cl:4][C:5]1[CH:10]=[C:9]([S:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:22])[CH2:20]Cl)=[CH:14][CH:13]=2)[CH:8]=[CH:7][C:6]=1[NH:23][C:24](=[O:35])[C:25]([O:31]C(=O)C)([CH3:30])[C:26]([F:29])([F:28])[F:27]>O.CC(C)=O>[Cl:4][C:5]1[CH:10]=[C:9]([S:11][C:12]2[CH:13]=[CH:14][C:15]([NH:18][C:19](=[O:22])[CH2:20][N:2]([CH3:3])[CH3:1])=[CH:16][CH:17]=2)[CH:8]=[CH:7][C:6]=1[NH:23][C:24](=[O:35])[C@:25]([OH:31])([CH3:30])[C:26]([F:28])([F:29])[F:27]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 22287497HCID 22287497, compound

Product 1

HCID 69752111HCID 69752111, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Dimethylamine (0.17 ml of a 40% solution in water) was added to a solution of (R)-N-{2-chloro-4-[4-(2-chloroacetylamino)phenylsulphanyl}phenyl -2-acetoxy-2-methyl-3,3,3-trifluoropropanamide (Method 19) (0.25 g) in acetone (1.5 ml). After 24 hours volatile material was removed by evaporation and the residue was dissolved in ethyl acetate, washed with water, and the organic layer was poured onto a Varian Chem Elut column. Elution with ethyl acetate gave the title compound (0.25 g) as a foam. NMR: 1.6 (s, 3H), 3.1 (s, 2H), 3.3 (s, 6H), 7.2 (d, 1H), 7.3 (s, 1H), 7.4 (d, 2H), 7.7 (m, 3H), 7.9 (d, 1H), 9.7 (s, 1H), 9.9 (s, 1H); MS (ESP−): 474.

Workup

  1. customAfter 24 hours volatile material was removed by evaporation
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. additionthe organic layer was poured onto a Varian Chem Elut column
  5. washElution with ethyl acetate

Sources & evidence

ORD record
ord-0c0bbef837e04fefafc2345bac8a9afd
Source dataset
uspto-grants-2002_12
Patent number
US06498275B1

Reaction notes

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