Water → HCID 15516568, compound

HRID 1244509Notes

Reaction equation

HRID 1244509 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 63.3%

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 g (4.96 mmol) of 4-nitrobenzylbromide. After ovemight stining, another portion (0.35 g; 1.65 mmol) of 4-nitrobenzylbrornide 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 MgSO, 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 MgSO
  4. filtrationfiltered
  5. customthe residue was purified by flash chromatography
  6. customThe pure fractions were collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4ce33c77f74942d7ba9655db7f17a9ea
Source dataset
uspto-grants-2006_10
Patent number
US07122535B2

Reaction notes

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