Water → HCID 2376813, compound

HRID 1480595Notes

Reaction equation

HRID 1480595 reaction equation
Cl[CH2:2][C:3]1[S:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH2:12]([O:14][C:15]1[CH:24]=[CH:23][C:18]2[N:19]=[C:20]([SH:22])[S:21][C:17]=2[CH:16]=1)[CH3:13].C(NC(C(C)C)(C(C)C)C)C.O>C1COCC1.CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[S:4]1[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=[C:3]1[CH2:2][S:22][C:20]1[S:21][C:17]2[CH:16]=[C:15]([O:14][CH2:12][CH3:13])[CH:24]=[CH:23][C:18]=2[N:19]=1

Participants

8

Reactant 4

HCID 962WaterHCID 3049782-(Chloromethyl)benzothiazoleHCID 21936557DiisopropyldiethylamineHCID 178466040HCID 178466040, compound

Product 1

HCID 2376813HCID 2376813, compoundYield 35%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The compound 2-(chloromethyl)benzothiazole [15] (1 g, 5.45 mmol), dissolved in THF (50 ml), was added drop-wise to a stirred solution of 4 (1.15 g, 5.45 mmol), N-ethyldiisopropylethylamine (1.35 ml, 8.17 mmol) and 4-dimethylaminopyridine (0.08 g, 0.545 mmol) in THF (50 ml). The reaction mixture was refluxed overnight. Then, the solution was cooled to room temperature, and water (100 ml) followed by chloroform (100 ml) were added. The organic layer was separated, washed twice in water, dried over sodium sulfate, filtered and evaporated. The crude solid was purified by column chromatography using 100% dichloromethane as an eluting solvent. The compound was obtained as dark brown solid. Yield 35%, m.p. 78-82° C. 1H NMR (DMSO-d6): δ 1.31-1.33 (t, 3H, J=3.45), 4.02-4.08 (q, 2H, J=6.9), 5.08 (s, 2H), 7.02-7.06 (dd, 1H, J=2.5, 6.3), 7.42-7.50 (m, 2H), 7.59-7.60 (d, 1H, J=2.4), 7.74-7.77 (d, 1H, J=9.0), 7.95-8.06 (dd, 2H, J=8.1, 15.3). 13C NMR (DMSO-d6): δ 14.8, 35.1, 64.1, 104.8, 115.6, 121.6, 122.3, 125.3, 126.2, 141.9, 143.1, 152.6, 165.6, 173.0, 178.4. MS: MW=358.50 g/mol, MH+=359.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. additionwere added
  3. customThe organic layer was separated
  4. washwashed twice in water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude solid was purified by column chromatography
  9. customThe compound was obtained as dark brown solid

Sources & evidence

ORD record
ord-7e3c553ae182456d9ec7bfe1581f1a04
Source dataset
uspto-grants-2016_08
Patent number
US09409904B2

Reaction notes

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