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

HRID 1112050Notes

Reaction equation

HRID 1112050 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 2-liter reaction flask with appropiate 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 1 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 2-liter reaction flask with appropiate 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-ebfc01c02eec418ea541fa07025601e0
Source dataset
uspto-grants-1978_10
Patent number
US04120690

Reaction notes

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