Water → HCID 21057621, compound

HRID 2216248Notes

Reaction equation

HRID 2216248 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Cl:11][C:12]1[C:13]([CH3:33])=[N:14][S:15][C:16]=1[NH:17][C:18](=[O:32])[CH2:19][C:20]1[CH:31]=[CH:30][C:23]2=[N:24][N:25]([CH2:27][CH2:28][CH3:29])[N:26]=[C:22]2[CH:21]=1.Cl[CH2:35][O:36][CH2:37][CH3:38].O>O1CCCC1>[Cl:11][C:12]1[C:13]([CH3:33])=[N:14][S:15][C:16]=1[N:17]([CH2:35][O:36][CH2:37][CH3:38])[C:18](=[O:32])[CH2:19][C:20]1[CH:31]=[CH:30][C:23]2=[N:24][N:25]([CH2:27][CH2:28][CH3:29])[N:26]=[C:22]2[CH:21]=1.[CH2:37]([O:36][CH2:35][N:14]1[CH:13]([CH3:33])[CH:12]([Cl:11])[C:16](=[N:17][C:18](=[O:32])[CH2:19][C:20]2[CH:31]=[CH:30][C:23]3=[N:24][N:25]([CH2:27][CH2:28][CH3:29])[N:26]=[C:22]3[CH:21]=2)[S:15]1)[CH3:38]

Participants

7

Reactant 4

HCID 962WaterHCID 18523Chloromethyl ethyl etherHCID 2733832Lithium HexamethyldisilazideHCID 21941238HCID 21941238, compound

Product 2

HCID 21057621HCID 21057621, compoundHCID 21941243HCID 21941243, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium bis(trimethylsilyl)amide (1.0 M solution in tetrahydrofuran, 3.3 ml, 0.0033 mol) was added dropwise to a solution of N-(4-chloro-3-methylisothiazol-5-yl)-(2-propylbenzotriazol-5-yl)acetamide (Compound No. A3.1) (0.699 g, 0.002 mol) in tetrahydrofuran (10 ml) and once the addition was complete the mixture was stirred at room temperature for 30 minutes. Chloromethylethyl ether (0.620 g, 0.0066 mol) was added and the mixture was stirred at room temperature for 2 hours. The mixture was poured into water, neutralised, and extracted with ethyl acetate. The organic extract was dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The residue was further purified by flash column chromatography, eluting initially with 2:1 hexane:ethyl acetate and then with ethyl acetate to give N-(4-chloro-3-methylisothiazol-5-yl)-N-(ethoxymethyl)-(2-propylbenzotriazol-5-yl)acetamide (0.135 g) as an orange gum and N-[2-ethoxymethyl-4-chloro-3-methylisothiazolin-5-ylidene]-(2-propylbenzotriazol-5-yl)-acetamide (0.128 g) as a colourless solid, m.p. 108–109° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. extractionneutralised, and extracted with ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate was evaporated in vacuo
  7. customThe residue was further purified by flash column chromatography
  8. washeluting initially with 2:1 hexane

Sources & evidence

ORD record
ord-070c829104ad445ca47515abc457e080
Source dataset
uspto-grants-2006_09
Patent number
US07112553B1

Reaction notes

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