Acetic Acid → HCID 21445640, compound

HRID 597570Notes

Reaction equation

HRID 597570 reaction equation
Br.[NH:2]=[C:3]1[N:7]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[NH:11][C:12](=[O:14])[CH3:13])[CH:6]=[CH:5][S:4]1.[C:18]([O-:21])(=O)[CH3:19].[K+].[C:23](OC(=O)C)(=O)[CH3:24].C(O)(=[O:32])C>>[C:18]([NH:2][CH:3]1[N:7]([CH2:8][C:17]([C:16]2[CH:15]=[C:10]([CH:9]=[CH:23][CH:24]=2)[NH:11][C:12](=[O:14])[CH3:13])=[O:32])[CH:6]=[CH:5][S:4]1)(=[O:21])[CH3:19]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 517044Potassium AcetateHCID 21445652HCID 21445652, compound

Product 1

HCID 21445640HCID 21445640, compound

Conditions

Temperature
50 °C

Procedure

A mixture of 35.6 g. (0.10 mole) of 3'-[2-imino-4-thiazolin-3-yl)acetanilide hydrobromide, (Example 2) 11.8 g. (0.12 mole) of potassium acetate, 150 ml. of acetic anhydride and 150 ml. of acetic acid is stirred at reflux for 1 hour. The mixture is cooled to 50° C., filtered, and the filtrate evaporated at reduced pressure. The residue is azeotroped with toluene, then triturated with 2-propanol and filtered to give 25.8 g. of crude product, which on recrystallization from aqueous acetic acid gives the product, melting point 224°-226° C. Anal. Calcd, for C15H15N3O3S: C, 56.77; H, 4.76; N, 13.24; S, 10.10. Found: C, 56.88; H, 4.77; N, 13.16; S, 9.90.

Workup

  1. additionA mixture of 35.6 g
  2. temperatureat reflux for 1 hour
  3. filtrationfiltered
  4. customthe filtrate evaporated at reduced pressure
  5. customThe residue is azeotroped with toluene
  6. customtriturated with 2-propanol
  7. filtrationfiltered
  8. customto give 25.8 g
  9. customof crude product, which on recrystallization from aqueous acetic acid
  10. customgives the product, melting point 224°-226° C

Sources & evidence

ORD record
ord-17255ca23f6544748d07e2b6bc73a49c
Source dataset
uspto-grants-1977_03
Patent number
US04014892

Reaction notes

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