4-Bromophenyl isocyanate → HCID 67354684, compound

HRID 525215Notes

Reaction equation

HRID 525215 reaction equation
[CH:1]1([C:4]([N:6]2[CH2:10][CH2:9][C@H:8]([CH2:11][C:12]([NH:14][NH2:15])=[O:13])[CH2:7]2)=[O:5])[CH2:3][CH2:2]1.[Br:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[O:25])=[CH:19][CH:18]=1.[N-]=C=O>ClCCl>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:15][NH:14][C:12](=[O:13])[CH2:11][C@H:8]2[CH2:9][CH2:10][N:6]([C:4]([CH:1]3[CH2:3][CH2:2]3)=[O:5])[CH2:7]2)=[O:25])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 756094-Bromophenyl isocyanateHCID 105034IsocyanateHCID 71087134HCID 71087134, compound

Product 1

HCID 67354684HCID 67354684, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a round bottom flask under nitrogen, a solution of 2-[(3R)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetohydrazide (2.16 mmol) in dichloromethane (5 mL) was cooled to 0° C. and 1-bromo-4-isocyanatobenzene (2.16 mmol) was added. Once the isocyanate dissolved, the cooling bath was removed and the reaction was allowed to warm to room temperature and was stirred for 3 h. The reaction was filtered to collect the white precipitate, washed with 10 mL cold dichloromethane, air dried for 1 h and then dried in a vacuum oven (60° C.) overnight to provide the title compound (88% yield). MS(ES)+ m/e 409.1, 411.1 [M+H]+.

Workup

  1. customthe cooling bath was removed
  2. filtrationThe reaction was filtered
  3. customto collect the white precipitate
  4. washwashed with 10 mL cold dichloromethane, air
  5. customdried for 1 h
  6. customdried in a vacuum oven (60° C.) overnight

Sources & evidence

ORD record
ord-60ac1398eeec4d6aaef92f732ff80e53
Source dataset
uspto-grants-2016_05
Patent number
US09340529B2

Reaction notes

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