3-Bromophenyl isocyanate → HCID 9977288, compound

HRID 2111962Notes

Reaction equation

HRID 2111962 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=[O:11].[Br:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N:20]=[C:21]=[O:22])[CH:15]=1>N1C=CC=CC=1.C(OCC)(=O)C>[Br:13][C:14]1[CH:15]=[C:16]([NH:20][C:21](=[O:22])[NH:1][C:2]2[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=2[CH2:9][C:10]([OH:12])=[O:11])[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 1410013-Bromophenyl isocyanateHCID 21689839(2-Amino-4-chlorophenyl)acetic acid

Product 1

HCID 9977288HCID 9977288, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Chlorooxindole (2.5 g, 14.9 mmol) was suspended in 50 ml 4 M aqueous NaOH and the mixture was refluxed for 6 hours. The reaction mixture was allowed to cool and the product precipitated and filtered off with suction. The solid was dissolved in water (100 ml) and precipitated with 4 M aqueous HCl at 0° C. The solid was then filtered with suction and dried under vacuum to yield 2.0 g (72%) of white crystalline solid. (2-Amino-4-chloro-phenyl)-acetic acid (700 mg, 3.8 mmol) was then dissolved in 25 ml pyridine and 1-bromo-3-isocyanato-benzene (811 mg, 4.1 mmol) was added drop-wise and the solution was stirred for 90 minutes. The reaction mixture was diluted with 150 ml ethyl acetate and washed twice with 1 M aqueous HCl. The organic phase was reduced under vacuum and the product recrystallised from ethyl acetate/heptane to yield 680 mg of white crystalline solid (47%) (m.p. 195-196° C.)

Workup

  1. washwashed twice with 1 M aqueous HCl
  2. customthe product recrystallised from ethyl acetate/heptane

Sources & evidence

ORD record
ord-e3214cc7dc6b4ce3b1bf10221fef32d0
Source dataset
uspto-grants-2009_04
Patent number
US07521480B2

Reaction notes

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