1-Hydroxybenzotriazole → HCID 18183833, compound

HRID 2205295Notes

Reaction equation

HRID 2205295 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl.CN.C[CH2:21][N:22]=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>O1CCCC1.C(N(CC)CC)C>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([NH:22][CH3:21])=[O:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 3015564'-Hydroxy-4-biphenylcarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6364545Methylamine hydrochloride

Product 1

HCID 18183833HCID 18183833, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

Into a 50-mL round-bottom flask was placed a solution of 4-(4-hydroxyphenyl)benzoic acid (1 g, 4.7 mmol, 1 equiv) in tetrahydrofuran (20 mL), methylamine hydrochloride, (0.409 g 6 mmol, 1.3 equiv), EDCl (1.18 g, 6.2 mmol, 1.3 equiv), HOBt (0.74 g, 5.5 mmol, 1.2 equiv), and triethylamine (2 mL). The resulting solution was stirred overnight at room temperature. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was purified by column chromatography on silica gel (eluting with 15:2 ethyl acetate/petroleum ether) to give 4-(4-hydroxyphenyl)-N-methylbenzamide as a white solid.

Workup

  1. customInto a 50-mL round-bottom flask was placed
  2. filtrationThe solids were filtered out
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. customThe residue was purified by column chromatography on silica gel (eluting with 15:2 ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-65c13170e8b545ccb2e2c3a50e4b1527
Source dataset
uspto-grants-2016_06
Patent number
US09371285B2

Reaction notes

Loading…