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Water → HCID 12803422, compound

HRID 371769
Notes
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Reaction equation

HRID 371769 reaction equation
[CH2:1](Br)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=O.C(Cl)(Cl)Cl.[CH3:15][O:16][CH2:17][CH2:18][NH2:19].C([N:22]([CH2:25]C)CC)C.[OH2:27]>>[CH3:15][O:16][CH2:17][CH2:18][N:19]1[CH:1]=[C:2]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:22][C:25]1=[O:27]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 962WaterHCID 6212Chloroform2×HCID 6259Phenacyl bromideHCID 80182-MethoxyethylamineHCID 8471Triethylamine

Product 1

HCID 12803422HCID 12803422, compound

Conditions

Temperature
0 °C

Procedure

Phenacyl bromide (199 g.), in 400 ml. of chloroform, is added over 1/2 hour to a mixture of 2-methoxyethylamine (82 g) and triethylamine (152 g.) in 200 ml. of chloroform at 0° C. The mixture is stirred for two hours at 0°-10° C. Water (400 ml.) is added and the organic layer is separated and washed with another 400 ml. of water. The chloroform layer is cooled to 0° C. with an ice bath and glacial acetic acid (72 g.) potassium cyanate (89 g.) and methanol (100 ml.) are added. The mixture is refluxed for ninety minutes, cooled and washed with saturated sodium bicarbonate solution, and the organic layer is dried over anhydrous sodium sulfate and then concentrated to give a semisolid. Trituration with 300 ml of ether and filtration gives the title product as a yellow crystal; m.p. 152°-154° C.

Workup

  1. customat 0° C
  2. customthe organic layer is separated
  3. washwashed with another 400 ml
  4. additionglacial acetic acid (72 g.) potassium cyanate (89 g.) and methanol (100 ml.) are added
  5. temperatureThe mixture is refluxed for ninety minutes
  6. temperaturecooled
  7. washwashed with saturated sodium bicarbonate solution
  8. dry with materialthe organic layer is dried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customto give a semisolid
  11. filtrationTrituration with 300 ml of ether and filtration

Sources & evidence

ORD record
ord-add380c4c62e4d2ea556bd3849492353
Source dataset
uspto-grants-1978_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04087611

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes