Ammonia → Acetamide, N-[[5-chloro-2-(hydroxymethyl)phenyl]phenylmethyl]-

HRID 1287705Notes

Reaction equation

HRID 1287705 reaction equation
C([O:4][CH2:5][C:6]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:7]=1[CH:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)C.[NH3:21].[CH2:22]([OH:24])[CH3:23]>>[Cl:20][C:17]1[CH:18]=[CH:19][C:6]([CH2:5][OH:4])=[C:7]([CH:8]([NH:21][C:22](=[O:24])[CH3:23])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:16]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 702EthanolHCID 12241060HCID 12241060, compound

Product 1

HCID 12241069Acetamide, N-[[5-chloro-2-(hydroxymethyl)phenyl]phenylmethyl]-

Conditions

Temperature
100 °C

Procedure

In a Parr bomb containing 47 g. of the compound of Example 5 in 200 ml. of ethanol, dry ammonia is introduced to a pressure of 5 atmospheres. After heating for 4 hours at 100° C., the resulting solution is evaporated. The oily residue is successively washed with light petroleum and diisopropyl ether, then it is taken up in a mixture of water and ethyl ether to give a solid which is used as such for the subsequent hydrolysis. Yield 16 g. A sample of the titular product crystallized from a mixture of ethyl ether and light petroleum melts at 131°-135° C.

Workup

  1. additionIn a Parr bomb containing 47 g
  2. customthe resulting solution is evaporated
  3. washThe oily residue is successively washed with light petroleum and diisopropyl ether
  4. additionit is taken up in a mixture of water and ethyl ether
  5. customto give a solid which
  6. customsuch for the subsequent hydrolysis
  7. customA sample of the titular product crystallized from a mixture of ethyl ether and light petroleum melts at 131°-135° C.

Sources & evidence

ORD record
ord-b3cab7c99fc74c3b859ae2e5c3332bbb
Source dataset
uspto-grants-1976_10
Patent number
US03985811

Reaction notes

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