Acetyl chloride → HCID 178473734, compound

HRID 446757Notes

Reaction equation

HRID 446757 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]3[N:25]4[C:19]([CH2:20][NH:21][CH2:22][C:23]5[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:24]=54)=[N:18][N:17]=3)[CH2:12][CH2:11]2)=[N:2]1.C(N(CC)CC)C.[C:38](Cl)(=[O:40])[CH3:39]>ClCCl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]3[N:25]4[C:19]([CH2:20][N:21]([C:38](=[O:40])[CH3:39])[CH2:22][C:23]5[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:24]=54)=[N:18][N:17]=3)[CH2:12][CH2:11]2)=[N:2]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178477855HCID 178477855, compound

Product 1

HCID 178473734HCID 178473734, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of trans-1-(4-benzo[d]isothiazol-3-yl-cyclohexyl)-8-chloro-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene (35 mg, 0.080 mmol) and triethylamine (0.022 ml, 0.16 mmol) in dichloromethane (0.8 ml) was added acetyl chloride (0.011 ml, 0.16 mmol) at room temperature. Stirring for 20 h was followed by partitioning between water (20 ml) and ethyl acetate (25 ml). The layers were separated. The organic layer was washed with two 25 ml-portions of water. The organic layer was concentrated in vacuo. Preparative RP-HPLC with water (0.05% formic acid)/methanol as eluent gave the title compound (26 mg, 68%) as white solid. MS m/e: 478 ([M+H]+)

Workup

  1. customby partitioning between water (20 ml) and ethyl acetate (25 ml)
  2. customThe layers were separated
  3. washThe organic layer was washed with two 25 ml-portions of water
  4. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-086aacda821541dcaa2d2dd9fedbcefb
Source dataset
uspto-grants-2013_07
Patent number
US08481528B2

Reaction notes

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