Thiourea → HCID 13826570, compound

HRID 1906608Notes

Reaction equation

HRID 1906608 reaction equation
Cl[CH2:2][C:3](=O)[CH2:4][C:5]([O:7][CH2:8][CH:9]=[CH2:10])=[O:6].[N:12]([O-:14])=O.[Na+].[NH2:16][C:17]([NH2:19])=[S:18]>C(O)(=O)C.O>[NH2:19][C:17]1[S:18][CH:2]=[C:3](/[C:4](=[N:12]/[OH:14])/[C:5]([O:7][CH2:8][CH:9]=[CH2:10])=[O:6])[N:16]=1

Participants

6

Reactant 3

HCID 2723790ThioureaHCID 13826568Prop-2-en-1-yl 4-chloro-3-oxobutanoateHCID 23668193Sodium Nitrite

Product 1

HCID 13826570HCID 13826570, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of 35.2 g of allyl 4-chloro-acetoacetate in 34 ml of acetic acid is treated dropwise within 45 minutes while stirring and cooling with a solution of 14.6 g of sodium nitrite in 21 ml of water. During the addition the temperature falls gradually from 0° C. to -15° C. The mixture is subsequently stirred at -15° C. for 2 hours. A solution of 15.2 g of thiourea in 120 ml of water, pre-warmed to 30° C., is treated with the resulting solution at such a rate that the temperature remains at about 30°-35° C. After stirring for an additional 7 hours, the crystalline precipitate obtained is filtered off, washed successively with water, acetonitrile and ether and crystallized from acetonitrile. There are obtained 21.8 g (48%) of allyl 2-(2-amino-4-thiazolyl)-2-(Z)-hydroxyimino-acetate of melting point 184°-185° C.

Workup

  1. additionDuring the addition the temperature
  2. customfalls gradually from 0° C. to -15° C
  3. stirringThe mixture is subsequently stirred at -15° C. for 2 hours
  4. additionis treated with the resulting solution at such a rate that the temperature
  5. customremains at about 30°-35° C
  6. stirringAfter stirring for an additional 7 hours
  7. customthe crystalline precipitate obtained
  8. filtrationis filtered off
  9. washwashed successively with water, acetonitrile and ether
  10. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-c56417f425494ba3a710c927d6ece1fc
Source dataset
uspto-grants-1987_03
Patent number
US04652651

Reaction notes

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