Thionyl Chloride → HCID 136084722, compound

HRID 44230Notes

Reaction equation

HRID 44230 reaction equation
[N:1]1[N:2]=[C:3]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25]O)=[CH:21][CH:20]=2)[N:4]2[C:10]=1[C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[NH:7][C:6]1[N:15]=[CH:16][CH:17]=[CH:18][C:5]2=1.S(Cl)([Cl:29])=O>ClCCl>[Cl:29][CH2:25][C:22]1[CH:21]=[CH:20][C:19]([C:3]2[N:4]3[C:5]4[CH:18]=[CH:17][CH:16]=[N:15][C:6]=4[NH:7][C:8]4[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=4[C:10]3=[N:1][N:2]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 136163785(4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)phenyl)methanol

Product 1

HCID 136084722HCID 136084722, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)phenyl)methanol (300 mg, 0.88 mmol) in dichloromethane (10 mL) was added thionyl chloride (excess, 1 mL) and the resulting solution was stirred at room temperature for 1 hour. The volatiles were removed in vacuo and the residue was carefully neutralized with a solution of sodium bicarbonate. The mixture was extracted with dichloromethane (3×25 mL) and the combined organics were dried over sodium sulfate, concentrated in vacuo. The 3-(4-(chloromethyl)phenyl)-9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepine was obtained as a yellow solid (317 mg, quantitative). M.p.=260-262° C.; 400 MHz 1H NMR (DMSO-d6) δ: 8.79 (s, 1H), 8.20 (dd, J=4.8, 1.6 Hz, 1H), 7.94 (dd, J=8.0, 1.6 Hz, 1H), 7.51 (d, J=8.8 Hz, 2H), 7.45-7.39 (m, 3H), 7.35-7.31 (m, 1H), 7.16-7.10 (m, 2H), 6.90 (dd, J=7.6, 4.8 Hz, 1H), 4.81 (s, 2H); LCMS [M+H]: 360.

Workup

  1. customThe volatiles were removed in vacuo
  2. extractionThe mixture was extracted with dichloromethane (3×25 mL)
  3. dry with materialthe combined organics were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1521dea19f4d4c17831d7c66b3c4d7ca
Source dataset
uspto-grants-2013_09
Patent number
US08541407B2

Reaction notes

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