Triethylamine → HCID 21285061, compound

HRID 365223

Reaction equation

HRID 365223 reaction equation
O[N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C(N(CC)CC)C.Cl[CH2:21][C:22]1[N:23]=[C:24]([NH:27][C:28]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[S:25][CH:26]=1.C(OCC)(=[O:49])C>C(#N)C.ClCCl>[C:28]([NH:27][C:24]1[S:25][CH:26]=[C:22]([CH2:21][O:49][C:8]2[CH:9]=[CH:10][CH:11]=[C:4]3[C:3]([NH:2][C:6](=[O:7])[C:5]=23)=[O:12])[N:23]=1)([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10665N-HydroxyphthalimideHCID 137451724-Chloromethyl-2-tritylaminothiazole

Product 1

HCID 21285061HCID 21285061, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

In 150 ml of acetonitrile was suspended 11.48 g of N-hydroxyphthalimide. To the suspension was added 7.11 g of triethylamine and dissoled therein. To the solution was added a solution of 27.5 g of 4-chloromethyl-2-tritylaminothiazole dissolved in 200 ml of dichloromethane and the mixture was stirred on an oil bath of 80° C. for 7 hours. The reaction mixture thus obtained was concentrated and the residue formed was dissolved in ethyl acetate. The solution was washed with water, dried by anhydrous magnesium sulfate, and concentrated. The residue was applied to column chromatography and the product was eluted with chloroform to provide 14.5 g of (2-tritylamino-4-thiazolyl)methoxyphthalimide.

Workup

  1. customThe reaction mixture thus obtained
  2. concentrationwas concentrated
  3. customthe residue formed
  4. washThe solution was washed with water
  5. dry with materialdried by anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. washthe product was eluted with chloroform

Sources & evidence

ORD record
ord-5c50afd2ec26496c93a45e7a11300628
Source dataset
uspto-grants-1986_08
Patent number
US04608373

Linked notes

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