Water → HCID 15516568, compound

HRID 2373774Notes

Reaction equation

HRID 2373774 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([C:16]2[N:17]=[C:18]([CH2:21][NH:22][CH3:23])[S:19][CH:20]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].CCN(CC)CC.[N+:31]([C:34]1[CH:41]=[CH:40][C:37]([CH2:38]Br)=[CH:36][CH:35]=1)([O-:33])=[O:32].O>C(Cl)Cl>[C:2]([C:5]1[CH:6]=[C:7]([C:16]2[N:17]=[C:18]([CH2:21][N:22]([CH3:23])[CH2:38][C:37]3[CH:40]=[CH:41][C:34]([N+:31]([O-:33])=[O:32])=[CH:35][CH:36]=3)[S:19][CH:20]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 660114-Nitrobenzyl bromide2×HCID 9865980HCID 9865980, compound2×

Product 1

HCID 15516568HCID 15516568, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cold solution of 1.1 g (3.31 mmol) of 4-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-N-methyl-2-thiazolemethanamine (Intermediate 58.3) and 0.7 ml (4.96 mmol) of Et3N in 50 ml CH2Cl2 was added portionwise 1.07 (4.96 mmol) of 4-nitrobenzylbromide. After overnight stirring, another portion (0.35 g; 1.65 mmol) of 4-nitrobenzylbromide was added. Twenty four hours later, the reaction mixture was poured into 100 ml of cold water and diluted with 50 ml CH2Cl2. The organic layer was decanted, washed with brine, dried over MgSO4 and filtered. The solvent was eliminated under reduced pressure and the residue was purified by flash chromatography using heptane/EtOAc (1/1) as eluent. The pure fractions were collected and concentrated to yield 0.98 g (63%) of a yellow solid. Melting point: 111.4-11.7° C.

Workup

  1. customThe organic layer was decanted
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe residue was purified by flash chromatography
  6. customThe pure fractions were collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fe7f26b0317b4f11ae32e0b91503f094
Source dataset
uspto-grants-2008_12
Patent number
US07459558B2

Reaction notes

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