3-Bromoaniline → HCID 59540876, compound

HRID 1677546Notes

Reaction equation

HRID 1677546 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.[C:9]([CH2:12][C:13]1([C:18](O)=[O:19])[CH2:17][CH2:16][S:15][CH2:14]1)(O)=[O:10].C(N1C=CN=C1)(N1C=CN=C1)=O>C1(C)C(C)=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:9](=[O:10])[CH2:12][C:13]3([CH2:14][S:15][CH2:16][CH2:17]3)[C:18]2=[O:19])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 115623-BromoanilineHCID 682631,1'-CarbonyldiimidazoleHCID 59540600HCID 59540600, compound

Product 1

HCID 59540876HCID 59540876, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 3-bromo-phenylamine (1.0 g, 5.81 mmol) and 3-carboxymethyl-tetrahydro-thiophene-3-carboxylic acid (1.15 g, 6.05 mmol, [Rice, L. M. et al; J. Med Chem; 6; 1963; 388-402]) in xylene (10 ml) was heated for 2 hours (oil bath, 180° C.) with fitted Dean-Stark trap to remove water. The material was cooled to ambient and the xylene stripped (rotovap/pump). The material was covered with dry CH2Cl2 (10 ml). Carbonyldiimidazole (1.18 g, 7.26 mmol) was added with vigorous stirring and a homogeneous solution was rapidly obtained. After over night stirring the material was adsorbed onto silica (12 g). The crude was purified by chromatography on silica gel, eluting with a gradient of 100% CH2Cl2 to 0.12% MeOH/CH2Cl2, to afford 1.76 g of 7-(3-bromo-phenyl)-2-thia-7-aza-spiro[4.4]nonane-6,8-dione as a light yellow solid.

Workup

  1. customto remove water
  2. temperatureThe material was cooled to ambient and the xylene
  3. customa homogeneous solution was rapidly obtained
  4. stirringAfter over night stirring the material
  5. customThe crude was purified by chromatography on silica gel
  6. washeluting with a gradient of 100% CH2Cl2 to 0.12% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-c524ba91c4b347b391f76cc59adcd51b
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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