2-(Dimethylamino)acetyl chloride hydrochloride → N-{3-[3-benzyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-4-oxothiazolidin-2-ylideneamino]phenyl}-2-dimethylaminoacetamide

HRID 1241992Notes

Reaction equation

HRID 1241992 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]=[C:9]2[N:13]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:12](=[O:21])[C:11](=[C:22]3[N:26]([CH3:27])[C:25]4[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=4[S:23]3)[S:10]2)[CH:5]=[CH:6][CH:7]=1.Cl.[CH3:33][N:34]([CH2:36][C:37](Cl)=[O:38])[CH3:35]>C(Cl)(Cl)Cl>[CH2:14]([N:13]1[C:12](=[O:21])[C:11](=[C:22]2[N:26]([CH3:27])[C:25]3[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=3[S:23]2)[S:10][C:9]1=[N:8][C:4]1[CH:3]=[C:2]([NH:1][C:37](=[O:38])[CH2:36][N:34]([CH3:35])[CH3:33])[CH:7]=[CH:6][CH:5]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 139949912-(Dimethylamino)acetyl chloride hydrochlorideHCID 72639856HCID 72639856, compound

Product 1

HCID 72639860N-{3-[3-benzyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-4-oxothiazolidin-2-ylideneamino]phenyl}-2-dimethylaminoacetamideYield 18%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-(3-aminophenylimino)-3-benzyl-5-(3-methyl-3H-benzothiazol-2-ylidene)thiazolidine-4-one (160 mg, 360 μmol) in chloroform (8 mL) was added N,N-dimethylaminoacetyl chloride hydrochloride (90 mg, 0.58 mmol) and TEA (150 μL, 1.1 mmol). The reaction solution was heated at reflux for 20 h, cooled, and concentrated in vacuo. The crude material was chromatographed (silica gel, 0–50% EtOAc/Hex) to give the title compound (34 mg, 18%) as a yellow solid. 1H-NMR (CDCl3): δ 9.03 (1H, s), 7.50 (2H, d), 7.37 (2H, t), 7.17–7.26 (5H, m), 7.11 (1H, m), 7.05 (1H, t), 6.88 (1H, d), 6.68 (1H, d), 5.03 (2H), 3.60 (3H, s), 3.00 (2H, s), 2.28 (6H, s); MS(ESI): 530(MH+).

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureat reflux for 20 h
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customThe crude material was chromatographed (silica gel, 0–50% EtOAc/Hex)

Sources & evidence

ORD record
ord-1ac23def45c94a6ba24e219fdd8ec276
Source dataset
uspto-grants-2006_10
Patent number
US07115640B2

Reaction notes

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