1,2-Dichloroethane → HCID 66611580, compound

HRID 2204698Notes

Reaction equation

HRID 2204698 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[C:8]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:7][C:3]=1[C:4](O)=[O:5].BrC1C(C=O)=CC(OCC2C=CC=CC=2)=C(C=1)C(OCC1C=CC=CC=1)=O.S(=O)(=O)(O)N.CC(CC)=C.[CH:66]([N:69](C(C)C)[CH2:70]C)(C)C.Cl.CNC.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>CN(C)C=O.O.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([C:4]([N:69]([CH3:70])[CH3:66])=[O:5])=[CH:7][C:8]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:9]([CH:10]=1)[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]

Participants

12

Reactant 8

HCID 111,2-DichloroethaneHCID 5987Sulfamic AcidHCID 10473Dimethylamine, hydrochlorideHCID 112402-Methyl-1-buteneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 66612057HCID 66612057, compoundHCID 86694927HCID 86694927, compound

Product 1

HCID 66611580HCID 66611580, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromo-5-[(phenylmethyl)oxy]-4-{[(phenylmethyl)oxy]carbonyl}benzoic acid (may be prepared as by oxidation of phenylmethyl 5-bromo-4-formyl-2-[(phenylmethyl)oxy]benzoate—may be prepared as described in Description 24—with sulfamic acid in the presence of 2-methyl-1-butene; 436 mg, 0.99 mmol) in N,N-dimethylformamide (5 ml) was added diisopropylethylamine (0.35 ml, 1.98 mmol), dimethylamine hydrochloride (121 mg, 1.48 mmol), 1-hydroxy-7-azabenzotriazole (188 mg, 1.38 mmol) and EDC (379 mg, 1.98 mmol). The solution was stirred for 18 hours. Ethyl acetate (10 ml) and water (10 ml) were added and the organic layer separated and washed further with water (2×10 ml), dried (MgSO4) and the solvent removed in vacuo. Purification by column chromatography (SiO2, 1:1 ethyl acetate/cyclohexane) gave the title compound as an orange gum. 195 mg.

Workup

  1. custommay be prepared
  2. customthe organic layer separated
  3. washwashed further with water (2×10 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customPurification by column chromatography (SiO2, 1:1 ethyl acetate/cyclohexane)

Sources & evidence

ORD record
ord-2bd32e0b85e6435183649db3ef5b0911
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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