4-Chlorobenzoyl chloride → HCID 20298375, compound

HRID 1389232Notes

Reaction equation

HRID 1389232 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17]CC)=[O:16])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C(N(C(C)C)C(C)C)C.[Cl:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1>C1C=CC=CC=1>[Cl:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([N:10]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[CH2:1][CH2:2][CH2:3]3)=[O:35])=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 20298347HCID 20298347, compound

Product 1

HCID 20298375HCID 20298375, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

6.3 g of ethyl 5-(indan-5-ylamino)valerate and 3.1 g of ethyl diisopropylamine are reacted in 50 ml of benzene with 4.2 g of p-chlorobenzoyl chloride. The resulting residue (left after filtering off the precipitate and concentrating the filtrate by evaporation) is saponified as described in Example 77b. Recrystallization of the crude product from ethyl acetate/petrol ether (1:2) yields 7.9 g (88.1% of theory) of 5-{p-chloro-[N-(indan-5-yl)]benzamido}valeric acid, MP 132° to 134°.

Workup

  1. waitThe resulting residue (left
  2. filtrationafter filtering off the precipitate
  3. concentrationconcentrating the filtrate
  4. customby evaporation)
  5. customRecrystallization of the crude product from ethyl acetate/petrol ether (1:2)

Sources & evidence

ORD record
ord-a0f27f6b649841ae91d8285e29610c07
Source dataset
uspto-grants-1981_01
Patent number
US04243678

Reaction notes

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