Acetyl chloride → HCID 70563701, compound

HRID 126926Notes

Reaction equation

HRID 126926 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([NH:8][C@H:9]2[C@@H:13]([OH:14])[CH2:12][N:11]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:10]2)=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:29](Cl)(=[O:31])[CH3:30]>O1CCCC1>[C:29]([NH:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([NH:8][C@H:9]2[C@@H:13]([OH:14])[CH2:12][N:11]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:10]2)=[O:7])=[CH:4][CH:3]=1)(=[O:31])[CH3:30]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 70563093HCID 70563093, compound

Product 1

HCID 70563701HCID 70563701, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6.0 g (0.02 mole) of cis-4-amino-N-(1-cyclohexyl-4-hydroxy-3-pyrrolidinyl)benzamide in 250 ml of tetrahydrofuran was mixed with 8 g of powdered anhydrous potassium carbonate and stirred while 1.6 g (0.02 mole) of acetyl chloride was added dropwise. The mixture was stirred for 18 hr. The tetrahydrofuran was removed and the residue was partitioned between water and chloroform. The chloroform was separated and in a short time the product precipitated. The precipitate was filtered and then triturated with boiling acetone, filtered and dried. The yield of product melting at 200.0°-203.0° C. was 5.1 g (74%).

Workup

  1. additionwas added dropwise
  2. customThe tetrahydrofuran was removed
  3. customthe residue was partitioned between water and chloroform
  4. customThe chloroform was separated and in a short time the product
  5. customprecipitated
  6. filtrationThe precipitate was filtered
  7. customtriturated with boiling acetone
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-98fb69b2fb6e4b349cc1b1ff4940a927
Source dataset
uspto-grants-1981_03
Patent number
US04254135

Reaction notes

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