Ammonium Hydroxide → HCID 52942521, compound

HRID 854932Notes

Reaction equation

HRID 854932 reaction equation
Cl[S:2]([OH:5])(=O)=[O:3].[Cl:6][C:7]1[CH:8]=[C:9]2[C:14](=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:16]=1)[O:13][CH:12]([C:23]([F:26])([F:25])[F:24])[C:11]([C:27]([OH:29])=[O:28])=[CH:10]2.[OH-].[NH4+:31]>CCOC(C)=O>[NH2:31][S:2]([C:20]1[CH:21]=[CH:22][C:17]([C:15]2[CH:16]=[C:7]([Cl:6])[CH:8]=[C:9]3[C:14]=2[O:13][CH:12]([C:23]([F:26])([F:24])[F:25])[C:11]([C:27]([OH:29])=[O:28])=[CH:10]3)=[CH:18][CH:19]=1)(=[O:5])=[O:3]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24638Chlorosulfonic acidHCID 21883549HCID 21883549, compound

Product 1

HCID 52942521HCID 52942521, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Chlorosulfonic acid (5 mL) was cooled to −20° C. and 6-chloro-8-phenyl-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid prepared as in U.S. Pat. No. 6,271,253 B1 Example 129, Step 2 (61.7 mg, 0.174 mmole) was added as a solid. The bright orange mixture was then added dropwise to a cold ammonium hydroxide solution, EtOAc was added and the mixture was stirred for 1 h. The EtOAc layer was separated, washed with H2O, aqueous NH4Cl, dried over Na2SO4, concentrated in vacuo and triturated with hexanes to give the product: 1H NMR (CD3OD/400 MHz) 7.95 (d, 2H, J=8.6 Hz), 7.81 (s, 1H), 7.66 (d, 2H, J=8.6 Hz), 7.46 (d, 1H, J=2.6 Hz), 7.42 (d, 1H, J=2.6 Hz), 5.80 (q, 1H, J=7.0 Hz); ESHRMS m/z 431.9945 (M−H, C17H10ClF3NO5S, Calc'd 431.9915).

Workup

  1. additionwas added
  2. customThe EtOAc layer was separated
  3. washwashed with H2O, aqueous NH4Cl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customtriturated with hexanes
  7. customto give the product

Sources & evidence

ORD record
ord-8224b8b32272461591e68c9a3e427298
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

Loading…