Diethyl Ether → HCID 88662945, compound

HRID 2308736Notes

Reaction equation

HRID 2308736 reaction equation
[CH:1]([O:14][C:15](=[O:44])/[C:16](/[C:19]1[N:20]=[C:21]([NH:24][C:25]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[S:22][CH:23]=1)=[N:17]\[OH:18])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:52][C:53]#[N:54].C(OCC)C>CS(C)=O>[CH:1]([O:14][C:15](=[O:44])/[C:16](=[N:17]\[O:18][CH2:52][C:53]#[N:54])/[C:19]1[N:20]=[C:21]([NH:24][C:25]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[S:22][CH:23]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 13386106HCID 13386106, compound

Product 1

HCID 88662945HCID 88662945, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In 70 ml of dimethylsulfoxide was dissolved 11.9 g (0.02 mole) of (Z)-2-(2-tritylamino-4-thiazolyl)-2-(hydroxyimino)acetic acid benzhydryl ester and after adding thereto 2.76 g of a powder of potassium carbonate and 1.7 g (0.0225 mole) of of chloroacetonitrile, the mixture was allowed to react overnight at room temperature. After the reaction was over, the reaction mixture was poured into 150 ml of ice water, the product was extracted first with 150 ml of ethyl acetate and then with 100 ml of ethyl acetate. The organic layers were collected, and washed twice with 50 ml of water and then with 10 ml of a saturated aqueous sodium chloride solution. The ethyl acetate layer obtained was dried over anhydrous magnesium sulfate, and the solvent was distilled off to provide a caramel. To the caramel was added 100 ml of ethyl ether to powder the caramel. 11.5 g (yield: 90.7%) of (Z)-2-(cyanomethyloxyimino)-2-(2-tritylamino-4-thiazolyl)acetic acid benzhydryl ester was obtained. ##STR15##

Workup

  1. additionafter adding
  2. customto react overnight at room temperature
  3. extractionthe product was extracted first with 150 ml of ethyl acetate
  4. customThe organic layers were collected
  5. washwashed twice with 50 ml of water
  6. customThe ethyl acetate layer obtained
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off
  9. customto provide a caramel

Sources & evidence

ORD record
ord-7e0622ce64754bbea88de480d254d598
Source dataset
uspto-grants-1987_09
Patent number
US04690921

Reaction notes

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