4-(5-Tert-butyl-1,3,4-thiadiazol-2-ylcarbamoylmethyl)-2-aminothiazole → 4-(5-Tert-butyl-1,3,4-thiadiazol-2-ylcarbamoylmethyl)-2-propionamidothiazole

HRID 1112055Notes

Reaction equation

HRID 1112055 reaction equation
[C:1]([C:5]1[S:9][C:8]([NH:10][C:11]([CH2:13][C:14]2[N:15]=[C:16]([NH2:19])[S:17][CH:18]=2)=[O:12])=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]>C(OC(=O)CC)(=O)CC>[C:1]([C:5]1[S:9][C:8]([NH:10][C:11]([CH2:13][C:14]2[N:15]=[C:16]([NH:19][C:11](=[O:12])[CH2:13][CH3:14])[S:17][CH:18]=2)=[O:12])=[N:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 213211484-(5-Tert-butyl-1,3,4-thiadiazol-2-ylcarbamoylmethyl)-2-aminothiazole

Product 1

HCID 213211654-(5-Tert-butyl-1,3,4-thiadiazol-2-ylcarbamoylmethyl)-2-propionamidothiazoleYield 67.2%

Reagents, catalysts & solvents 1

HCID 31263Propionic anhydrideSolvent

Procedure

A mixture of 4.8 g (0.016 mole) of 4-(5-tert-butyl-1,3,4-thiadiazol-2-ylcarbamoylmethyl)-2-aminothiazole dissolved 20 ml of propionic anhydride was heated for 1 hour at 90°. The reaction solution was cooled and the precipitate was collected. The crude solid was recrystallized from chloroform-hexane. There was obtained 1.9 g of product, m.p. 210°-12°. N.M.R. (CDCl3) ∂ 1.1-1.4 (CH3, triplet), 1.4 [C(CH3)3 ], 2.3-2.7 (CH2, quartet), 3.9 (CH2, singlet), 6.8 (hetero-aromatic).

Workup

  1. temperaturewas heated for 1 hour at 90°
  2. temperatureThe reaction solution was cooled
  3. customthe precipitate was collected
  4. customThe crude solid was recrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-4999d11f3850410e8c3a78f2d811abe0
Source dataset
uspto-grants-1978_10
Patent number
US04120690

Reaction notes

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