1-Hydroxybenzotriazole → 1-(hexanoyloxy)methyl N-[2-[3-chloro-4-(2-methylbenzoyl)-phenylamino]phenyl]carbamate

HRID 2182584Notes

Reaction equation

HRID 2182584 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[CH:23]=[CH:22][C:12]([C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[O:14])=[C:11]([Cl:24])[CH:10]=1.[C:25](=O)([O:36]C1C=CC([N+]([O-])=O)=CC=1)[O:26][CH2:27][O:28][C:29](=[O:35])[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].ON1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C>CN(C=O)C>[Cl:24][C:11]1[CH:10]=[C:9]([NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][C:25](=[O:36])[O:26][CH2:27][O:28][C:29](=[O:35])[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:23]=[CH:22][C:12]=1[C:13](=[O:14])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 98191574-(2-Aminophenylamino)-2-chloro-2'-methylbenzophenoneHCID 15053076Hexanoyloxymethyl p-nitrophenyl carbonate2×

Product 1

HCID 224805051-(hexanoyloxy)methyl N-[2-[3-chloro-4-(2-methylbenzoyl)-phenylamino]phenyl]carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(2-aminophenylamino)-2-chloro-2′-methylbenzophenone (305 mg, 1.0 mmol) and hexanoyloxymethyl 4-nitrophenyl carbonate (Compound 207) (3.3 g, 10 mmol) in DMF (50 ml) was added 1-hydroxybenzotriazole (270 mg, 2.0 mmol) followed by N-ethyl di-iso-propylamine (0.18 ml, 1.05 mmol). The reaction mixture was stirred at room temperature. After 72 hours, the reaction mixture was poured into ice/water and extracted with diethylether. The etheral extracts were washed with a saturated sodium carbonate solution, water, and brine and dried over anhydrous sodium sulphate. Filtration and concentration in vacuo afforded the crude product. This was further purified by chromatography using Et2O/hexane 2:1 as eluent.

Workup

  1. extractionextracted with diethylether
  2. washThe etheral extracts were washed with a saturated sodium carbonate solution, water, and brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-bf845b4dc4194778ab4c00f75341460e
Source dataset
uspto-grants-2005_05
Patent number
US06897236B1

Reaction notes

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