Thiourea → 5-(2-Amino-4-thiazolyl)-1,3-dihydro-2H-indol-2-one

HRID 2414110Notes

Reaction equation

HRID 2414110 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)=O.[NH2:15][C:16]([NH2:18])=[S:17]>CCO>[NH2:18][C:16]1[S:17][CH:2]=[C:3]([C:5]2[CH:6]=[C:7]3[C:11](=[CH:12][CH:13]=2)[NH:10][C:9](=[O:14])[CH2:8]3)[N:15]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 220993095-(Bromoacetyl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 26087615-(2-Amino-4-thiazolyl)-1,3-dihydro-2H-indol-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-(α-bromoacetyl)oxindole (5 g) and thiourea (1.67 g) in absolute EtOH (250 ml) is refluxed for 30 minutes. The reaction mixture is cooled to RT, filtered, and washed with absolute EtOH affording the desired product. The free base is converted to its methanesulfonate salt by the procedure previously described in Example 12, affording the desired product, M.P.=244°-246° C.

Workup

  1. filtrationfiltered
  2. washwashed with absolute EtOH affording the desired product

Sources & evidence

ORD record
ord-3b586d910641479c91ccb9d565a2c5aa
Source dataset
uspto-grants-1988_01
Patent number
US04721721

Reaction notes

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