Sodium Chloride → HCID 178444264, compound

HRID 463912Notes

Reaction equation

HRID 463912 reaction equation
N([O-])=O.[Na+].[C:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C@H:20]3[CH2:25][CH2:24][C@H:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:22][CH2:21]3)=[CH:16][C:15]=2N)=[CH:10][CH:9]=1)(=[O:7])[CH3:6].[Na+].[Cl-:33].[O-]S([O-])=O.[Na+].[Na+]>O.Cl>[C:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C@H:20]3[CH2:25][CH2:24][C@H:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:22][CH2:21]3)=[CH:16][C:15]=2[Cl:33])=[CH:10][CH:9]=1)(=[O:7])[CH3:6]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 24437Sodium SulfiteHCID 23668193Sodium NitriteHCID 178444265HCID 178444265, compound

Product 1

HCID 178444264HCID 178444264, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent2×

Procedure

A solution of 7.2 g of NaNO2 in 25 ml of water is added to a suspension of 36.7 g of 4'-acetyl-2-amino-4-(trans-4-pentylcyclohexyl)-biphenyl in 150 ml of 15% aqueous hydrochloric acid at -5° in the course of 0.5 hours. The solution thus obtained is added dropwise, at 0°-5° in the course of 1 hour, to a Cu(I) salt solution which has been prepared from 25 g of CuSO4.5H2O, 8.8 g of NaCl, 6.3 g of Na2SO3, 100 ml of water and 40 ml of 32% hydrochloric acid. After the mixture has been heated to 40° for half an hour, it is cooled and extracted with CH2Cl2 and the product is worked up in the customary manner. 4'-Acetyl-2-chloro-4-(trans-4-pentylcyclohexyl)-biphenyl is obtained.

Workup

  1. customThe solution thus obtained
  2. temperatureAfter the mixture has been heated to 40° for half an hour
  3. temperatureit is cooled
  4. extractionextracted with CH2Cl2

Sources & evidence

ORD record
ord-43cb55e5b8fe4e6b9e9d285fd8971b8c
Source dataset
uspto-grants-1985_10
Patent number
US04544771

Reaction notes

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