Chloroform → HCID 66899545, compound

HRID 2036888Notes

Reaction equation

HRID 2036888 reaction equation
Br.[CH3:2][O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH2:11][NH:10][CH2:9]2)=[O:5].C(N(CC)CC)C.[C:22]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:27]=[CH:26][C:25]([C:28](Cl)=[O:29])=[CH:24][CH:23]=1.C(Cl)(Cl)Cl>C1COCC1>[CH3:2][O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH2:11][N:10]([C:28]([C:25]1[CH:26]=[CH:27][C:22]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[CH:23][CH:24]=1)=[O:29])[CH2:9]2)=[O:5]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 841514-Phenylbenzoyl chlorideHCID 86656619HCID 86656619, compound

Product 1

HCID 66899545HCID 66899545, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,3-Dihydro-1H-isoindole-5-carboxylic acid methyl ester compound with hydrobromic acid (0.80 g), triethylamine (1.30 mL) and biphenyl-4-carbonyl chloride (0.67 g) are stirred in THF (35 mL) at ambient temperature. After 1.5 h the mixture is treated with CHCl3 washed, dried and evaporated until a solid starts to separate. The product is fully crystallized by adding heptane. 0.94 g of the title compound is obtained with MP 172-180° C.

Workup

  1. washwashed
  2. customdried
  3. customevaporated until a solid starts
  4. customto separate
  5. customThe product is fully crystallized
  6. additionby adding heptane

Sources & evidence

ORD record
ord-aed167949bc74f2b915840772eb5391c
Source dataset
uspto-grants-2013_11
Patent number
US08575193B2

Reaction notes

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