Hydrochloric Acid → HCID 20298346, compound

HRID 1389229Notes

Reaction equation

HRID 1389229 reaction equation
[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].[Cl:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1.Cl>[OH-].[Na+]>[Cl:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([N:7]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:27])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 85014-Chlorobenzoyl chlorideHCID 20298406HCID 20298406, compound

Product 1

HCID 20298346HCID 20298346, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

5.4 g of 5-[N-(biphenyl-2-yl)amino]valeric acid is dissolved in 40 ml of 0.2 N caustic soda solution. Into the resulting clear solution (while vigorously stirring and constantly controlling the pH) 3.5 g of p-chlorobenzoyl chloride is added, drop by drop, while concurrently adding dilute caustic soda solution in order to maintain the pH at between 7 and 8. After the addition of acid chloride is complete, the solution is stirred for a further 30 minutes at pH 8 and then acidified to pH 3 with dilute hydrochloric acid. The precipitate, which is oily at first crystallizes after a time. It is filtered off and recrystallized from isopropyl alcohol to obtain 7.6 g (93% of thoery) of 5-[p-chloro-N-(biphenyl-2-yl)benzamido]valeric acid, MP 170° to 173°, which is identical with the compound obtained by the procedure of Example 53.

Workup

  1. additionis added
  2. temperatureto maintain the pH at between 7 and 8
  3. stirringthe solution is stirred for a further 30 minutes at pH 8
  4. customat first crystallizes after a time
  5. filtrationIt is filtered off
  6. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-1027064c2fa148b799149979e5081eb7
Source dataset
uspto-grants-1981_01
Patent number
US04243678

Reaction notes

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