Trityl chloride → Ethyl 2-oxo-2-(2-(tritylamino)thiazol-4-yl)acetate

HRID 1395044Notes

Reaction equation

HRID 1395044 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=1.[C:21]1([C:27]([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)Cl)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C)C=O.C(Cl)Cl>[C:21]1([C:27]([NH:8][C:9]2[S:10][CH:11]=[C:12]([C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=2)([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 4356513Ethyl 2-(2-Amino-4-thiazolyl)-2-oxoacetate

Product 1

HCID 13151727Ethyl 2-oxo-2-(2-(tritylamino)thiazol-4-yl)acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

27 g of triethylamine are added to a solution of 90 g of ethyl 2-aminothiazol-4-glyoxylate in 225 ml of dimethylformamide and 375 ml of CH2Cl2, at -15°, and 75 g of triphenylchloromethane are then added at -30 °. After 15 minutes at -30°, the mixture is stirred for 3 hours without a cooling bath, 500 ml of CH2Cl2 are added to the resulting reaction mixture and the mixture is washed with 300 ml of 1 N HCl and then twice with 200 ml of water, The organic phase is dried over Na2SO4 and the solvent is evaporated off. An oil remains and this was used for the further reactions without prior purification.

Workup

  1. washthe mixture is washed with 300 ml of 1 N HCl
  2. dry with materialtwice with 200 ml of water, The organic phase is dried over Na2SO4
  3. customthe solvent is evaporated off
  4. custompurification

Sources & evidence

ORD record
ord-bee8114c3cd848cd9e23b03e449a8104
Source dataset
uspto-grants-1980_05
Patent number
US04201779

Reaction notes

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