m-Toluidine → HCID 842193, compound

HRID 1247460Notes

Reaction equation

HRID 1247460 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.CCN=C=NCCCN(C)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=2)=[O:11])=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 7934m-ToluidineHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 74654Benzeneacetic acid, 4-bromo-HCID 757711-Hydroxybenzotriazole

Product 1

HCID 842193HCID 842193, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-bromophenylacetic acid (502 mg, 2.33 mmol), m-toluidine (0.25 mL, 2.33 mmol), HOBT (350 mg, 2.59 mmol), and N-methylmorpholine (0.51 mL, 4.64 mmol) in DMF (10 mL) was treated with EDCI (496 mg, 2.59 mmol), stirred overnight at room temperature, and poured into ice water. The resulting white precipitate was collected by filtration to give 672 mg of the desired product. MS (ESI(+)) m/e 304, 306 (M+H)+.

Workup

  1. filtrationThe resulting white precipitate was collected by filtration

Sources & evidence

ORD record
ord-72e92d6059ce4be89ac58819a4a2395f
Source dataset
uspto-grants-2006_10
Patent number
US07129260B2

Reaction notes

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