Water → HCID 22105454, compound

HRID 358039Notes

Reaction equation

HRID 358039 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:12][C:11](=[O:13])[CH2:10][CH2:9]S(=O)(=O)[CH:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[C:6]=2[CH:23]=1.C(O)(C)(C)C.O>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:12][C:11](=[O:13])[CH2:10][CH:9]=[C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[C:6]=2[CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6386tert-ButanolHCID 20449977HCID 20449977, compound

Product 1

HCID 22105454HCID 22105454, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
35 °C

Procedure

67.0 g of 8-chloro-6-(2-fluorophenyl)-1,3,4,6-tetrahydro-2-oxo-2H-5,1-benzothiazocine 5,5-dioxide are suspended in a mixture of 670 ml of carbon tetrachloride, 670 ml of t-butanol and 31.5 ml of water. The suspension is pre-warmed to 35° C. There are then rapidly added thereto while cooling four 51.5 g portions of potassium t-butylate (the temperature amounts to 45°-50°). The mixture is stirred for a further 35 minutes, the temperature dropping to about 35°. The mixture is poured on to ice, whereupon it is extracted with methylene chloride. The organic phase is evaporated and the residue is triturated with ether. The crystalline product is filtered off. There is obtained 7-chloro-5-(2-fluorophenyl)-1,3-dihydro-2H-1-benzazepin-2-one of melting point 214°-215°.

Workup

  1. additionThere are then rapidly added
  2. customamounts to 45°-50°
  3. customdropping to about 35°
  4. additionThe mixture is poured on to ice, whereupon it
  5. extractionis extracted with methylene chloride
  6. customThe organic phase is evaporated
  7. customthe residue is triturated with ether
  8. filtrationThe crystalline product is filtered off

Sources & evidence

ORD record
ord-ef4cddb03ffb4a1787733283cb4904f8
Source dataset
uspto-grants-1984_08
Patent number
US04464300

Reaction notes

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