O-Xylene → N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)acetoacetamide

HRID 261758Notes

Reaction equation

HRID 261758 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.C1(C)C(C)=CC=CC=1.[NH2:15][C:16]1[S:17][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[N:19][N:20]=1>CCCCCCC>[C:21]([C:18]1[S:17][C:16]([NH:15][C:4](=[O:5])[CH2:3][C:2]([CH3:1])=[O:6])=[N:20][N:19]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 12661DiketeneHCID 170170Buthidazolamine

Product 1

HCID 21321160N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)acetoacetamideYield 58.9%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

A two-liter reaction flask with appropriate fittings was charged with 33.6 g (0.4 mole) of diketene, 965 ml of xylene and 59.7 g (0.38 mole) of 2-amino-5-tert butyl-1,3,4-thiadiazole. The stirred mixture was heated to 70° at which time all solids had dissolved. After one hour, the solution was cooled and added to 2500 ml of chilled heptane. Product precipitation was judged complete after two hours. The solids were collected on a vacuum filter and air dried. There was obtained 54 g (58.9%) of white product, m.p. 166°-68°. N.M.R. (CDCl3 -dimethyl-d6 sulfoxide) ∂ 1.5 [C(CH3)3 ], 2.0 (CH3, enol), 2.3 (CH3, keto), 3.6 (CH2), 5.4 (CH, enol).

Workup

  1. customA two-liter reaction flask with appropriate fittings
  2. temperatureThe stirred mixture was heated to 70° at which time all solids
  3. dissolutionhad dissolved
  4. temperaturethe solution was cooled
  5. customProduct precipitation
  6. waitwas judged complete after two hours
  7. customThe solids were collected on a vacuum
  8. filtrationfilter
  9. customair dried

Sources & evidence

ORD record
ord-e6febb9c83974ff4bd5a4cba987fe684
Source dataset
uspto-grants-1979_05
Patent number
US04152329

Reaction notes

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