Ethyl isocyanate → HCID 86737121, compound

HRID 1759296Notes

Reaction equation

HRID 1759296 reaction equation
[CH2:1]([OH:26])[CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]#[C:8][CH2:9][CH2:10][C:11]#[C:12][C:13]#[C:14][CH2:15][CH2:16][C:17]#[C:18][C:19]#[C:20][CH2:21][CH2:22][CH2:23][CH2:24][OH:25].[CH2:27]([N:29]=[C:30]=[O:31])[CH3:28].O1CC[CH2:34][CH2:33]1>>[CH2:27]([N:29]([CH2:33][CH3:34])[C:30]([O:25][CH2:24][CH3:23])=[O:31])[CH3:28].[CH2:24]([OH:25])[CH2:23][CH2:22][CH2:21][C:20]#[C:19][C:18]#[C:17][CH2:16][CH2:15][C:14]#[C:13][C:12]#[C:11][CH2:10][CH2:9][C:8]#[C:7][C:6]#[C:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:26]

Participants

4

Reactant 3

HCID 8022Ethyl isocyanateHCID 8028TetrahydrofuranHCID 20165401HCID 20165401, compound

Product 1

HCID 86737121HCID 86737121, compound

Procedure

Following the general procedure of Example 1, 1.3 parts CF4 diol, 40 parts tetrahydrofuran, 1.42 parts ethyl isocyanate, 0.2 parts DBTE, and 4 parts TEA were mixed together and allowed to react at room temperature for 11/2 hours. The product was precipitated by the addition of 175 parts n-hexane and was quickly filtered and washed several times with additional n-hexane. After drying, the 2.3 parts of product XLV was obtained representing a 35.8% conversion. The product had a fluffy texture which changes blue very rapidly when exposed to daylight. The product was recrystallized by dissolving in 40 parts hot acetone followed by 20 parts hot petroleum ether. The precipitate turned blue during crystallization at about -8° C. The melting point of the material was 146.4° to 148.8° C.

Workup

  1. additionwere mixed together
  2. customto react at room temperature for 11/2 hours
  3. customThe product was precipitated by the addition of 175 parts n-hexane
  4. filtrationwas quickly filtered
  5. washwashed several times with additional n-hexane
  6. customAfter drying
  7. customthe 2.3 parts of product XLV was obtained
  8. customThe product was recrystallized
  9. dissolutionby dissolving in 40 parts hot acetone
  10. customThe precipitate turned blue during crystallization at about -8° C
  11. customwas 146.4° to 148.8° C.

Sources & evidence

ORD record
ord-7a93a969faa34e5aa9daf195d17fe034
Source dataset
uspto-grants-1982_07
Patent number
US04339951

Reaction notes

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