Trityl chloride → HCID 22273507, compound

HRID 1064329Notes

Reaction equation

HRID 1064329 reaction equation
[C:1]1([C:7](Cl)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][C:22]1[NH:23][CH:24]=[C:25]([CH2:27][CH2:28][OH:29])[N:26]=1.C(N(CC)CC)C>CN(C=O)C>[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:23]2[CH:24]=[C:25]([CH2:27][CH2:28][OH:29])[N:26]=[C:22]2[CH3:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178432806HCID 178432806, compound

Product 1

HCID 22273507HCID 22273507, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Triphenylmethyl chloride (24.5 g, 88 mmol) in DMF (100 ml) was added dropwise over 1 hr to a solution of 2-methyl-4-(2-hydroxyethyl)imidazole (10 g, 80 mmol) and triethylamine in DMF (100 ml). The reaction mixture was stirred at ambient temperature for 18 hours and then the volatiles were removed by evaporation. The resultant solid was triturated with water (3×500 ml) and ether (200 ml), collected by filtration and dried under vacuum at 60° C. to give the title compound (23.7 g, 80%) as a pale yellow solid. NMR 1.43 (d, 3H), 1.62 (s, 3H), 2.53 (s, 1H), 4.80 (q, 1H), 6.59 (s, 1H), 7.13 (m, 6H), 7.37 (m, 9H); m/z 369.

Workup

  1. customthe volatiles were removed by evaporation
  2. customThe resultant solid was triturated with water (3×500 ml) and ether (200 ml)
  3. filtrationcollected by filtration
  4. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-111673b9a9ae42faa4eb69ded850d7ef
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

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