Ammonia → HCID 86711153, compound

HRID 625180Notes

Reaction equation

HRID 625180 reaction equation
[Cl:1][C:2]1[C:8]2[CH:9]=[CH:10][C:11]([C:13](Cl)=[O:14])=[CH:12][C:7]=2[S:6][C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]=2[N:3]=1.O1CCOCC1.[NH3:26]>ClCCl>[Cl:1][C:2]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([NH2:26])=[O:14])=[CH:12][C:7]=2[S:6][C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 86711154HCID 86711154, compound

Product 1

HCID 86711153HCID 86711153, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 11-chloro-dibenzo[b,f][1,4]thiazepine-3-carbonyl chloride, prepared as described in the previous step, (ca 1.5 mmol) in dichloromethane (10 mL) was treated with a 1,4-dioxane solution of ammonia (0.5 M, 9 mL) under ice bath. The resulting suspension was stirred at room temperature for 1 hour, and the reaction was quenched with water (10 mL). The resulting precipitate was filtered, washed with water and dichloromethane, and dried. The organic layer of the filtrate was washed with saturated aqueous sodium bicarbonate solution and concentrated to additional off white product, which was used in the next step without additional purification. LC-MS: m/z 289 (M+1). 1H NMR (DMSO-d6, 400 MHz): δ (ppm) 8.19 (br, 1H), 8.00-7.96 (m, 2H), 7.90 (d, 1H), 7.64 (br, 1H), 7.56 (m, 1H), 7.47 (m, 1H), 7.31 (m, 2H).

Workup

  1. customthe reaction was quenched with water (10 mL)
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water and dichloromethane
  4. customdried
  5. washThe organic layer of the filtrate was washed with saturated aqueous sodium bicarbonate solution
  6. concentrationconcentrated to additional off white product, which
  7. customwas used in the next step without additional purification

Sources & evidence

ORD record
ord-07d6ab5d50174953a0a6bae0fe356385
Source dataset
uspto-grants-2016_04
Patent number
US09304126B2

Reaction notes

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