Methyl chloroformate → HCID 20375741, compound

HRID 1448811Notes

Reaction equation

HRID 1448811 reaction equation
C(OC([NH:8][CH:9]1[CH2:14][CH:13]=[CH:12][C:11]([C:15]([OH:17])=O)=[CH:10]1)=O)(C)(C)C.C(N(CC)CC)C.[Cl:25]C(OC)=O.[CH2:30]([NH2:33])[CH2:31][CH3:32]>ClCCl>[ClH:25].[CH2:30]([NH:33][C:15]([C:11]1[CH:12]=[CH:13][CH2:14][CH:9]([NH2:8])[CH:10]=1)=[O:17])[CH2:31][CH3:32]

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 7852PropylamineHCID 8471TriethylamineHCID 20375744HCID 20375744, compound

Product 1

HCID 20375741HCID 20375741, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 240 mg (1 m mole) of 3-tert-butoxycarbonylamino-1,5-cyclohexadiene carboxylic acid in 5 ml of dichloromethane is treated with 202 mg (2 m mole) of triethylamine and 94 mg (1 m mole) of methyl chloroformate. After 30 minutes at 25° C. the solution is treated with 60 mg (1 m mole) of n-propylamine for 1 hour at 25° C. after which the solution is diluted with dichloromethane, washed with water, dryed and evaporated. The residue is stirred for 18 hours in 7 ml of methanol and 3.5 ml of 5% aqueous HCl. Evaporation affords N-propyl-3-amino-1,5-cyclohexadienecarboxamide hydrochloride.

Workup

  1. washwashed with water
  2. customevaporated
  3. customEvaporation

Sources & evidence

ORD record
ord-b4dd171cba0f42f2986533649ac2121d
Source dataset
uspto-grants-1980_02
Patent number
US04187316

Reaction notes

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