Phosgene → HCID 72547173, compound

HRID 1506857Notes

Reaction equation

HRID 1506857 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([C:11]([NH:13][NH2:14])=[O:12])[O:8][C:7]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[C:6]=2[CH:27]=1.[C:28](Cl)(Cl)=[O:29]>C1(C)C=CC=CC=1.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([C:11]3[O:12][C:28](=[O:29])[NH:14][N:13]=3)[O:8][C:7]([CH:21]3[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]3)([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[C:6]=2[CH:27]=1

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 89907187HCID 89907187, compound

Product 1

HCID 72547173HCID 72547173, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 300 mg 6-chloro-4,4-dicyclohexyl-4H-benzo[1,3]dioxine-2-carboxylic acid hydrazide in 4.3 ml toluene was added 4 ml of a 1.9M solution of phosgene in toluene. The reaction mixture was heated to reflux for 4 h. After cooling to room temperature, the reaction mixture was diluted with EtOAc, washed with water and brine and dried with MgSO4. Then the solvent was removed in vacuo and the crude product purified by preparative HPLC (C18 reverse phase column, elution with water/MeCN gradient with 0.1% TFA). The fractions containing the product were evaporated and lyophilized to yield a solid. Yield: 180 mg.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 h
  3. washwashed with water and brine
  4. dry with materialdried with MgSO4
  5. customThen the solvent was removed in vacuo
  6. customthe crude product purified by preparative HPLC (
  7. washC18 reverse phase column, elution with water/MeCN gradient with 0.1% TFA)
  8. additionThe fractions containing the product
  9. customwere evaporated
  10. customto yield a solid

Sources & evidence

ORD record
ord-479f2cd043c74a8f9ec2267ac2ce0959
Source dataset
uspto-grants-2015_12
Patent number
US09221784B2

Reaction notes

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