4,5-Dihydro-2-thiazolamine → 3'-[(2-Imino-3-thiazolidinyl)acetyl]acetanilide hydrobromide

HRID 1729856Notes

Reaction equation

HRID 1729856 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][CH2:18][CH2:19][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])[CH2:19][CH2:18][S:17]1

Participants

4

Reactant 2

HCID 156894,5-Dihydro-2-thiazolamineHCID 124318473'-Acetamido-2-bromoacetophenone

Product 1

HCID 214456433'-[(2-Imino-3-thiazolidinyl)acetyl]acetanilide hydrobromide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 5.12 g. (0.020 mole) of 3'-bromoacetylacetanilide in 70 ml. of acetone is added to a stirred solution of 2.04 g. (0.020 mole) of 2-amino-2-thiazoline in 30 ml. of acetone. The mixture is stirred 1.5 hours and the precipitate then filtered, washed with acetone and dried to give 6.00 g. of white solid, which on recrystallization from water gives the product, melting point 275°-277°C. Anal. Calcd. for C13H16BrN3O2S: C, 43.58; H, 4.50; Br, 22.31; N, 11.73; S, 8.95. Found: C, 43.99; H, 4.66; Br, 22.51; N, 11.72; S, 9.14.

Workup

  1. filtrationthe precipitate then filtered
  2. washwashed with acetone
  3. customdried
  4. customto give 6.00 g
  5. customof white solid, which on recrystallization from water
  6. customgives the product, melting point 275°-277°C

Sources & evidence

ORD record
ord-ae2b07d164464c2cac887900a770965e
Source dataset
uspto-grants-1976_11
Patent number
US03989835

Reaction notes

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