Dichloromethane → HCID 4081485, compound

HRID 894449Notes

Reaction equation

HRID 894449 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:13][O:14][CH3:15])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1.C(Cl)Cl.[C:19](Cl)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl.C(N(CC)CC)C>CO.O.C(N(CC)CC)C>[C:19]([NH:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:13][O:14][CH3:15])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 6456Trityl chlorideHCID 11130Triethylamine hydrochlorideHCID 581091Ethyl 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate

Product 1

HCID 4081485HCID 4081485, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 3.41 kg of the product of Step C, 17 liters of methylene chloride and 2.275 liters of triethylamine was stirred for 15 minutes and then 4.55 kg of trityl chloride were added at 20°-25° C. over one hour with stirring under nitrogen. The mixture was stirred for 20 hours at 20°-25° C. under nitrogen during which triethylamine hydrochloride crystallized and the mixture was washed with 10.2 liters of iced 0.5 N hydrochloric acid and twice with 10.2 liters of iced demineralized water and the wash waters were extracted with 1.7 liters of methylene chloride. The combined organic extracts were dried and filtered and the filter was washed with 1.7 liters of methylene chloride. The filtrates were evaporated to dryness under reduced pressure below 50° C. to obtain 8.425 kg of raw product. The latter was dissolved at 20°-25° C. in 8.4 liters of methanol and the solution was stirred for an hour at 20°-25° C. after the addition of 2.8 liters of demineralized water to induce crystallization. The mixture was stirred for another hour and was vacuum filtered. The product was empasted twice with 1.7 liters of methanol containing 25% water and was dried at 40° C. to obtain 7.165 kg of the syn isomer of ethyl 2-(2-tritylamino-4-thiazolyl)-2-methoxyiminoacetate which was identical to the product of Example 3, Step B.

Workup

  1. stirringwith stirring under nitrogen
  2. customcrystallized
  3. washthe mixture was washed with 10.2 liters of iced 0.5 N hydrochloric acid and twice with 10.2 liters of iced demineralized water
  4. extractionthe wash waters were extracted with 1.7 liters of methylene chloride
  5. customThe combined organic extracts were dried
  6. filtrationfiltered
  7. washthe filter was washed with 1.7 liters of methylene chloride
  8. customThe filtrates were evaporated to dryness under reduced pressure below 50° C.
  9. customto obtain 8.425 kg of raw product
  10. stirringthe solution was stirred for an hour at 20°-25° C.
  11. customcrystallization
  12. stirringThe mixture was stirred for another hour
  13. filtrationfiltered
  14. customwas dried at 40° C.

Sources & evidence

ORD record
ord-003cfd9f682a4db2898f8427484da3df
Source dataset
uspto-grants-1981_08
Patent number
US04283396

Reaction notes

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