Water → (2Z)-2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-trityloxyiminoacetic acid

HRID 378520Notes

Reaction equation

HRID 378520 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:11]/[O:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)/[C:8]([OH:10])=[O:9])[N:6]=1.[Cl:32]N1C(=O)CCC1=O.O>CN(C=O)C>[NH2:1][C:2]1[S:3][C:4]([Cl:32])=[C:5](/[C:7](=[N:11]/[O:12][C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)/[C:8]([OH:10])=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 10117176(Z)-2-(2-Aminothiazol-4-yl)-2-((trityloxy)imino)acetic acid

Product 1

HCID 10600185(2Z)-2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-trityloxyiminoacetic acidYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (Z)-2-(2-aminothiazol-4-yl)-2-(triphenylmethoxyimino)ace tic acid (5.81 g, 13.47 mmol) in DMF (30 mL) at room temperature (1 mL) was added N-chlorosuccinimide (1.80 g, 13.47 mmol). After overnight reaction the reaction mixture was poured into water (about 500 mL) and the resulting precipitate was filtered, washed with water and then with ethyl acetate and dried in vacuum to afford 4.43 g (71%) of the title compound. 13C NMR (CDCl3) δ108.5 , 125.6 ,126.2 , 126.6 , 12.3 , 134.7 141.8, 146.5 , 162.1 , 163.3.

Workup

  1. customAfter overnight reaction the reaction mixture
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with water
  4. dry with materialwith ethyl acetate and dried in vacuum

Sources & evidence

ORD record
ord-d0663932306b4dc88414bed87dda4e1f
Source dataset
uspto-grants-2000_02
Patent number
US06030965

Reaction notes

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