Acetyl chloride → HCID 21427238, compound

HRID 1606663Notes

Reaction equation

HRID 1606663 reaction equation
[CH3:1][NH:2][C:3](=[O:23])[CH:4]([CH2:21][OH:22])[NH:5][C:6](=[O:20])[C:7]1[C:12]([I:13])=[C:11]([NH2:14])[C:10]([I:15])=[C:9]([C:16]([OH:18])=[O:17])[C:8]=1[I:19].[CH3:24][C:25](N(C)C)=[O:26].C(Cl)(=O)C>O>[CH3:1][NH:2][C:3](=[O:23])[CH:4]([CH2:21][OH:22])[NH:5][C:6](=[O:20])[C:7]1[C:12]([I:13])=[C:11]([NH:14][C:25](=[O:26])[CH3:24])[C:10]([I:15])=[C:9]([C:16]([OH:18])=[O:17])[C:8]=1[I:19]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 31374DimethylacetamideHCID 21427255HCID 21427255, compound

Product 1

HCID 21427238HCID 21427238, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

82.4 g. (0.125 mole) of N-(3-carboxy-5-amino-2,4,6-triiodobenzoyl)-DL-serine methylamide (IV b), m.p. 259°-260° C. (decomposition), is dissolved in 200 ml. of dimethylacetamide; under agitation, 33.4 ml. of acetyl chloride is added dropwise thereto. The reaction mixture is agitated for 20 hours, mixed with 40 ml. of water, and, after another 30 minutes of agitation, concentrated under vacuum. The residue is stirred overnight with 150 ml. of water, the precipitate is vacuum-filtered, stirred in 150 ml. of 1N sodium hydroxide solution with the addition of 15 ml. of 37% strength sodium hydroxide solution and activated carbon for 2 hours, the activated carbon is removed, and the filtrate is brought to pH 1 with concentrated hydrochloric acid. After allowing the reaction mixture to stand overnight at 0° C., the precipitate is vacuum-filtered, washed with ice water, and dried under vacuum at 70° C.

Workup

  1. additionmixed with 40 ml
  2. concentrationconcentrated under vacuum
  3. stirringThe residue is stirred overnight with 150 ml
  4. filtrationof water, the precipitate is vacuum-filtered
  5. stirringstirred in 150 ml
  6. additionof 1N sodium hydroxide solution with the addition of 15 ml
  7. customfor 2 hours
  8. customthe activated carbon is removed
  9. waitto stand overnight at 0° C.
  10. filtrationthe precipitate is vacuum-filtered
  11. washwashed with ice water
  12. customdried under vacuum at 70° C.

Sources & evidence

ORD record
ord-ca9c05e0ab584c759fc4fc09c2aee0f6
Source dataset
uspto-grants-1976_04
Patent number
US03953501

Reaction notes

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