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Water → HCID 13338941, compound

HRID 653309
Notes
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Reaction equation

HRID 653309 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:12]/[OH:13])/[C:8]([O:10][CH3:11])=[O:9])[N:6]=1.C(N(CC)CC)C.[C:21](Cl)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CN(C)C=O>[C:21]([NH:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:12]/[OH:13])/[C:8]([O:10][CH3:11])=[O:9])[N:6]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 6411353Methyl 2-amino-alpha-(hydroxyimino)thiazol-4-acetate

Product 1

HCID 13338941HCID 13338941, compound

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Conditions

Temperature
-30 °C

Procedure

In 10 ml of N,N-dimethylformamide is dissolved 4.62 g of methyl 2-(2-amino-4-thiazolyl)-(Z)-2-hydroxyiminoacetate, followed by addition of 3 ml of triethylamine. Then, under stirring at -30° C., 6.42 g of trityl chloride is added over one hour. The mixture is further stirred at that temperature for one hour and, then at 15° C. for an additional 2 hours. To this reaction mixture is added 200 ml of water, followed by extraction with 200 ml of ethyl acetate. The ethyl acetate extract is washed twice with 200 ml portions of water and dried over anhydrous sodium sulfate. The solvent is then distilled off. The residue is purified by column chromatography [silica gel: 100 g; eluent:hexane-ethyl acetate (1:1)] and the resultant crystals are recrystallized from ethyl acetate to give methyl 2-(2-tritylamino-4-thiazolyl)-(Z)-2-hydroxyiminoacetate as colorless granules, m.p. 294°-205° C.

Workup

  1. stirringThe mixture is further stirred at that temperature for one hour
  2. extractionfollowed by extraction with 200 ml of ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washis washed twice with 200 ml portions of water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent is then distilled off
  7. customThe residue is purified by column chromatography [silica gel: 100 g; eluent:hexane-ethyl acetate (1:1)]
  8. customthe resultant crystals are recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-61b47f39c26547beba384a95f25edf72
Source dataset
uspto-grants-1987_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04675397

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes