Hydrochloric Acid → 2-(2-(2-Aminothiazol-4-yl)ethyl)isoindoline-1,3-dione hydrochloride

HRID 2247929Notes

Reaction equation

HRID 2247929 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([N:9]([CH2:12][CH2:13][C:14]([CH2:16]Br)=O)[C:10](=[O:11])[C:4]2=[CH:3][CH:2]=1)=[O:8].[NH2:18][C:19]([NH2:21])=[S:20].[ClH:22]>C(O)CC>[CH:1]1[CH:6]=[C:5]2[C:7]([N:9]([CH2:12][CH2:13][C:14]3[N:18]=[C:19]([NH2:21])[S:20][CH:16]=3)[C:10](=[O:11])[C:4]2=[CH:3][CH:2]=1)=[O:8].[ClH:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723790ThioureaHCID 37597442-(4-Bromo-3-oxobutyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 441183012-(2-(2-Aminothiazol-4-yl)ethyl)isoindoline-1,3-dione hydrochloride

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

1-Bromo-4-N-phthalimido-2-butanone (50.0 g, 0.169 mol) and thiourea (25.71 g, 0.338 mol) were mixed with n-propanol (1000 ml) and concentrated hydrochloric acid (100 ml), and the reaction mixture was heated to reflux for 1.5 hour. After cooling, the precipitate was filtered and washed with n-propanol and ether. After air drying, the title product was obtained as a fluffy white solid (37.51 g, 0.121 mol, 72% yield), m.p. 230°-240° (decomp.).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 1.5 hour
  3. temperatureAfter cooling
  4. filtrationthe precipitate was filtered
  5. washwashed with n-propanol and ether
  6. customAfter air drying

Sources & evidence

ORD record
ord-799a2794326549a88fe2587ce8766e2f
Source dataset
uspto-grants-1991_08
Patent number
US05037834

Reaction notes

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