Acetone → N-(1-cyclohexylmethyl-3-pyrrolidinyl)-2-methoxy-4-amino-5-ethylsulphinyl benzamide

HRID 652780Notes

Reaction equation

HRID 652780 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([NH:12]C(C)=O)[C:9]([S:16]([CH2:18][CH3:19])=[O:17])=[CH:8][C:4]=1[C:5]([OH:7])=O.CC(C)=O.ClC(OCC(C)C)=O.[CH:32]1([CH2:38][N:39]2[CH2:43][CH2:42][CH:41]([NH2:44])[CH2:40]2)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>O.C(N(CC)CC)C>[CH:32]1([CH2:38][N:39]2[CH2:43][CH2:42][CH:41]([NH:44][C:5](=[O:7])[C:4]3[CH:8]=[C:9]([S:16]([CH2:18][CH3:19])=[O:17])[C:10]([NH2:12])=[CH:11][C:3]=3[O:2][CH3:1])[CH2:40]2)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 62365Isobutyl chloroformateHCID 218906401-(Cyclohexylmethyl)pyrrolidin-3-amineHCID 541097612-Methoxy-4-acetamino-5-ethylsulphinyl benzoic acid

Product 1

HCID 20196856N-(1-cyclohexylmethyl-3-pyrrolidinyl)-2-methoxy-4-amino-5-ethylsulphinyl benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

8.5 g of 2-methoxy-4-acetamino-5-ethylsulphinyl benzoic acid, 70 ml of acetone, 10 ml of water and 3 g of triethylamine are placed in a 250 ml flask fitted with an agitator, a thermometer and a dropping funnel. The solution is cooled to about 0° C., after which 4.2 g of isobutyl chloroformate is poured in drop by drop. It is agitated for 45 minutes at 0° C. then 6 g of 1-cyclohexylmethyl-3-amino-pyrrolidine is dripped in. It is reacted for 2 hours at room temperature, 50 ml of water is added and the acetone is evaporated under vacuum. 10 ml of soda and 50 ml of water are added to the aqueous residue and it is heated to reflux for 5 hours then cooled. The suspension is extracted twice with 50 ml of methylene chloride, and the organic phase is dried over magnesium sulphate and filtered. The filtrate is evaporated dry under vacuum, and the residue is dissolved in 70 ml of hot ethyl acetate. The product is re-crystallised by cooling and filtered. It is washed with a little ether and dried in an oven at 50° C.

Workup

  1. customfitted with an agitator
  2. customIt is reacted for 2 hours at room temperature
  3. customthe acetone is evaporated under vacuum
  4. addition10 ml of soda and 50 ml of water are added to the aqueous residue and it
  5. temperatureis heated
  6. temperatureto reflux for 5 hours
  7. temperaturethen cooled
  8. extractionThe suspension is extracted twice with 50 ml of methylene chloride
  9. dry with materialthe organic phase is dried over magnesium sulphate
  10. filtrationfiltered
  11. customThe filtrate is evaporated
  12. customdry under vacuum
  13. dissolutionthe residue is dissolved in 70 ml of hot ethyl acetate
  14. customThe product is re-crystallised
  15. temperatureby cooling
  16. filtrationfiltered
  17. washIt is washed with a little ether
  18. customdried in an oven at 50° C.

Sources & evidence

ORD record
ord-c6804a728d31412ca4fdd5c1fae1716c
Source dataset
uspto-grants-1987_06
Patent number
US04673686

Reaction notes

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