Dichloromethane → HCID 22119844, compound

HRID 1274650Notes

Reaction equation

HRID 1274650 reaction equation
[OH:1][CH2:2][C:3]1[C:7]2[CH:8]=[C:9]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]3=[O:24])[CH:10]=[CH:11][C:6]=2[S:5][N:4]=1.C(Cl)Cl.C(N(C(C)C)C(C)C)C.[CH2:37]([O:39][CH2:40]Cl)[CH3:38]>CCOCC>[CH2:37]([O:39][CH2:40][O:1][CH2:2][C:3]1[C:7]2[CH:8]=[C:9]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:21])([F:20])[F:22])[N:14]([CH3:23])[C:13]3=[O:24])[CH:10]=[CH:11][C:6]=2[S:5][N:4]=1)[CH3:38]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 18523Chloromethyl ethyl etherHCID 81531DiisopropylethylamineHCID 221198213-[3-(hydroxymethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 22119844HCID 22119844, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 3-[3-(hydroxymethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (0.800 g, 0.00224 mol) and methylene chloride is added ethyldiisopropylamine (0.780 ml, 0.00448 mol) followed by chloromethyl ethyl ether (0.310 ml, 0.00336 mol). The resultant mixture is stirred 42.5 hours at room temperature, diluted with ether, washed sequentially with 1 M aqueous hydrochloric acid, saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to a yellow syrup. The syrup is chromatographed on silica gel with hexanes:ethyl acetate to give the product as a white solid which is identified by NMR spectral analysis.

Workup

  1. washwashed sequentially with 1 M aqueous hydrochloric acid, saturated sodium bicarbonate and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo to a yellow syrup
  5. customThe syrup is chromatographed on silica gel with hexanes

Sources & evidence

ORD record
ord-ddb3fbe77182416c926ff1265cfa9adf
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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