2-Aminothiazole → 3'-[(2-Imino-4-thiazolin-3-yl)acetyl]acetanilide hydrobromide

HRID 597568Notes

Reaction equation

HRID 597568 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[NH:8][C:9](=[O:11])[CH3:10])=[O:4].[NH2:15][C:16]1[S:17][CH:18]=[CH:19][N:20]=1>CC(C)=O>[BrH:1].[NH:15]=[C:16]1[N:20]([CH2:2][C:3]([C:5]2[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=2)[NH:8][C:9](=[O:11])[CH3:10])=[O:4])[CH:19]=[CH:18][S:17]1

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 124318473'-Acetamido-2-bromoacetophenone

Product 1

HCID 215015883'-[(2-Imino-4-thiazolin-3-yl)acetyl]acetanilide hydrobromide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 64.8 g. (0.253 mole) of 3'-bromoacetyl acetanilide (Example 1) and 25.3 g. (0.253 mole) of 2-aminothiazole in 450 ml. of acetone is heated at 50°-60° C for 2 hours. The precipitated product is filtered, washed with acetone and dried to give 58.74 g. of crude product which on recrystallization from methanol-ether gives the product melting point 225° dec. Anal. Calcd, for C13H14BrH3O2S: C, 43.83; H, 3.96; Br, 22.43; N, 11.80; S, 9.00. Found: C, 43.90; H, 4.21; Br, 22.21; N, 11.73; S, 8.69.

Workup

  1. filtrationThe precipitated product is filtered
  2. washwashed with acetone
  3. customdried
  4. customto give 58.74 g
  5. customof crude product which on recrystallization from methanol-ether

Sources & evidence

ORD record
ord-3d0e90b0c59f4a7d9091b3851b1e09a0
Source dataset
uspto-grants-1977_03
Patent number
US04014892

Reaction notes

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