Cyanomethyl carbamimidothioate--hydrogen chloride (1/1) → HCID 14456852, compound

HRID 1649759Notes

Reaction equation

HRID 1649759 reaction equation
Cl.[C:2]([CH2:4][S:5]C(=N)N)#[N:3].C[O-].[Na+].[C:12]([NH:31][C:32]1[S:33][CH:34]=[C:35](/[C:37](=[N:43]/[O:44][CH2:45][CH2:46]I)/[C:38]([O:40][CH2:41][CH3:42])=[O:39])[N:36]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C=O>[C:12]([NH:31][C:32]1[S:33][CH:34]=[C:35](/[C:37](=[N:43]/[O:44][CH2:45][CH2:46][S:5][CH2:4][C:2]#[N:3])/[C:38]([O:40][CH2:41][CH3:42])=[O:39])[N:36]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 108839Cyanomethyl carbamimidothioate--hydrogen chloride (1/1)HCID 10942334Sodium MethoxideHCID 12884454HCID 12884454, compound

Product 1

HCID 14456852HCID 14456852, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-35 °C

Procedure

In 10 ml of dimethylformamide is suspended 0.976 g of S-cyanomethylisothiourea hydrochloride prepared according to the method described in Japanese Published Unexamined Patent Application No. 50-154279. Under cooling at -35° C. and stirring, 2.73 g of 28% (w/w) sodium methylate solution is added dropwise, after which the mixture is stirred at -40° C. to -35° C. for 10 minutes. Then, a solution of 3.94 g of ethyl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(2-iodoethoxyimino)acetate in 10 ml of dimethylformamide is added at the same temperature. The mixture is stirred at or below -30° C. for 5 minutes and then under ice-cooling for 4 hours. The reaction mixture is poured into 400 ml of ice-water and extracted with ethyl acetate. The extract is washed with aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. To the solid residue is added a mixture of ether-petroleum ether (1:1) and the mixture is filtered to give 3.18 g of ethyl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(2-cyanomethylthioethoxyimino)acetate as light yellow crystals.

Workup

  1. customprepared
  2. stirringafter which the mixture is stirred at -40° C. to -35° C. for 10 minutes
  3. stirringThe mixture is stirred at or below -30° C. for 5 minutes
  4. temperatureunder ice-cooling for 4 hours
  5. extractionextracted with ethyl acetate
  6. washThe extract is washed with aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. additionTo the solid residue is added
  10. additiona mixture of ether-petroleum ether (1:1)
  11. filtrationthe mixture is filtered

Sources & evidence

ORD record
ord-293af3b2f49e4640b602ccaf98dcfcf3
Source dataset
uspto-grants-1990_05
Patent number
US04921851

Reaction notes

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