Sulfuric Acid → HCID 21486044, compound

HRID 1414917Notes

Reaction equation

HRID 1414917 reaction equation
[CH3:1][N:2]([CH3:26])[C:3](=[O:25])[C:4]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:5]1[CH2:9][CH2:8][N:7](C(C)C)[CH2:6]1.C(Cl)(Cl)=O.C(N(CC)CC)C.C(Cl)(=O)N.S(=O)(=O)(O)O>C1C=CC=CC=1>[CH3:26][N:2]([CH3:1])[C:3](=[O:25])[C:4]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH:5]1[CH2:9][CH2:8][NH:7][CH2:6]1

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 6371PhosgeneHCID 8471TriethylamineHCID 68048Carbamic chlorideHCID 21486054HCID 21486054, compound

Product 1

HCID 21486044HCID 21486044, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution containing 25.2 g. (0.0720 mole) of N,N-dimethyl-α,α-diphenyl-α-(1-isopropyl-3-pyrrolidinyl)acetamide, 14.3 g. (0.153 mole) of phosgene, and 7.27 g. (0.0720 mole) of triethylamine in 275 ml. of benzene was stirred at room temperature for one hour. After extraction with dilute acid the benzene layer produced 25.6 g. of neutral material which showed a good carbamoyl chloride band at 5.85 μ. The material was hydrolyzed in refluxing 10% sulfuric acid for one hour to give 19.5 g. of crude product. Acid-base extraction removed some neutral material and the free base was converted to the fumarate salt which was recrystallized from ethanol-isopropyl ether; m.p. 159°-160° C.

Workup

  1. additionA solution containing 25.2 g
  2. extractionAfter extraction
  3. additionwith dilute acid the benzene layer
  4. customproduced 25.6 g
  5. customto give 19.5 g
  6. extractionAcid-base extraction
  7. customremoved some neutral material
  8. customwas recrystallized from ethanol-isopropyl ether

Sources & evidence

ORD record
ord-281d229674f84acd82bf6299158a6890
Source dataset
uspto-grants-1977_01
Patent number
US04002766

Reaction notes

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